


play it again, sam

by let_them_be_happy



Category: Supernatural
Genre: Alternate Universe - 1940s, Alternate Universe - Casablanca Fusion, Alternate Universe - Mob, Alternate Universe- No Supernatural, Angst with a Happy Ending, Bartender Castiel (Supernatural), F/M, Gen, Historical Inaccuracy, Lawyer Sam Winchester, M/M, Mobster Castiel, POV Alternating, Private Investigator Dean, but like ex-mobster castiel, i'm just putting it there to be safe, inaccurate descriptions of violence, really vague descriptions of violence, sort of, vaguely casablanca au, wish me luck kiddos cause this is a rewrite
Language: English
Status: Completed
Published: 2017-06-04
Updated: 2017-11-03
Packaged: 2018-11-09 06:06:42
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 8
Words: 21,127
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11098482
Author URL: https://archiveofourown.org/users/let_them_be_happy/pseuds/let_them_be_happy
Summary: It starts off innocently, like these types of things always do. In this case, it’s an innocuous statement made by one of the regulars in Castiel Novak’s bar, made in the day’s dying light.“My brother’s coming into town.”-It's funny how one sentence seems to turn Castiel's life upside down.





	1. he walks into mine

It starts off innocently, like these types of things always do. In this case, it’s an innocuous statement made by one of the regulars in Castiel Novak’s bar, made in the day’s dying light.

“My brother’s coming into town.”

Were Castiel a lesser man, he wouldn’t be there at the moment, but that’s not important. What is important is that Castiel manages not to drop the glass he’s drying with a rag. “Isn’t that a good thing?” he asks, his voice miraculously steady, looking up from his hands into the face of one Sam Winchester.

Sam smiles sadly at the drink in his hands, running one finger around the glass’s rim. “Not with Dean. He’s always in some kind of trouble - or some kind of trouble’s following him.” Castiel nods understandingly, putting the now-clean glass down in order to refill Sam’s drink. Sam offers the bartender a quick smile in thanks before taking a sip of whiskey. “Bobby - the mechanic, Bobby Singer - he told me on my way over.” Sam shakes his head with another smile. “Gotta give it to the old man, he knows how to give you some bad news.”

Castiel frowns, Sam’s words mixed with his tone confusing the bartender. “Do you not like Mister Singer? I’ve heard he’s a good man.”

Sam waves Castiel’s concern away with a free hand. “Bobby’s a good man. I don’t mean that I don’t like him, Castiel, I just mean that he’s not one to pull his punches.” It’s another few moments before and with another smile that Sam speaks again. “I think you and Dean would get along.”

It’s been said that Castiel has a very good poker face, which he is currently using at this moment. “I knew a man named Dean once,” Castiel says, even though he starts cursing himself for it the moment the words leave his mouth. Luckily he didn’t say something as obvious as “I knew your brother,” otherwise Sam would’ve perked up even more than he already has.

As it is, Sam’s interest is more then piqued, since Castiel almost never talks about his past and when he does, it’s vague and unsatisfying at best. Castiel is tempted to compare the young lawyer to a puppy, what with the way his head shoots up from his glass and he sits up straighter. “You did?” Sam leans further onto the counter, and Castiel can almost see Dean beside his brother, encouraging the mischief in the younger Winchester’s eyes. “What was he like?”

Castiel almost says, “Well, much like your brother.” What he actually says is, “He was infuriatingly stubborn. I only knew him for a short time, though it was stretched over a period of several months. Any time we interacted face to face, there was something irritating but somehow charming in his behavior.” A cough sounds from the other side of the bar, closer to the door, and Castiel remembers himself. “It was a long time ago, and no longer of any importance.”

Sam opens his mouth to question further - Castiel can almost hear Dean saying _damn lawyer kid_ \- but a series of gunshots stops him before any of his questions get voiced. The two of them, along with everyone else in the bar, turn their heads to the bar’s door to try to see what’s going on. “Damn mobsters,” Sam mutters as Castiel walks out from around the bar and towards the door. Before he has the chance to take more than a few steps towards the door, gunshots fly in through the open doorway, and Castiel throws himself behind the nearest table. When he turns to look at Sam, he’s unsurprised to find the Winchester with his pistol out, crouched behind a table parallel to Castiel. “You good?” Sam asks when he sees Castiel looking at him.

Castiel nods, wishing to all hell he had his own gun on him. “Are you injured?” Sam shakes his head, indicating the negative. Castiel nods again before looking around the bar to see if any of his other patrons are injured. For the most part, they just look a little terrified, so Castiel feels justified in getting them out of there. “Sam, get everyone else out of here.” Sam looks like he’s about to argue, but Castiel holds up a hand. “I am more than capable of handling whatever these mobsters might have in store.”

Finally, Sam nods, though he looks less than happy to be agreeing with Castiel in these circumstances. In the lull before the next round of gunfire, Sam manages to get the rest of the bar’s patrons gathered and on their way out the back of the bar. Internally, Castiel suppresses a sigh. There goes a few customers he’ll probably never get back. The closest weapon Castiel has available is the knife he uses to slice up fruit for people who want fruit with their drinks, so he grabs it from its place behind the bar before continuing to the door.

The gunshots pick up again, this time much closer to the bar, though from the sound of it, at least one of the participants of this gunfight is heading _towards_ Castiel’s bar for cover. Castiel resists the urge to roll his eyes - he isn’t a goddamn angel and his middle name isn’t Charity.

Still, when Castiel catches a glimpse of the dumbass who’s trying to use his bar as a sanctuary, he has to force himself to focus on the very angry mobsters headed his way and not on the shocking familiarity of said dumbass. Castiel feels very justified when the man runs into the bar only to run into Sam, who knocks the man out without so much as a glance to confirm that he _should_ be knocking the man out. That distraction taken care of, Castiel reaches the door and stands in the doorway, his arms by his sides and his grip on the knife casual.

Apparently deeming it safe, the mobsters crawl out from behind the nearby buildings, converging in the street in front of Castiel’s bar. Judging by the awful scent of rotten eggs, Castiel hazards a guess that these gun-happy kids belong to Crowley, the local mob boss. Now Castiel doesn’t bother holding back in rolling his eyes. He’s heard of Crowley before he moved here, way back when he was actually involved in all this mob business, when Crowley was still climbing the ranks and nowhere near being the boss. Castiel can only guess what business Crowley’s got with this man in particular.

One of the slimeballs occupying the space in front of Castiel’s bar steps out of the group, towards Castiel, and Castiel thinks that this must be the one dumb enough to try to scare him. “You the owner of this little place?” Head Goon asks, and Castiel senses more than hears Sam taking up a defensive position behind him, fully prepared to open fire if he thinks Castiel needs the help.

With another internal sigh, Castiel shifts on his feet to block Sam’s shot. Like he told the younger Winchester, he’s more than capable of handling these children. “I am,” Castiel says, answering Head Goon’s question even as he hears Sam’s almost silent huff of frustration. “What of it?”

Head Goon nods his head into the bar. “Got somethin’ in there that don’t belong to you.” Castiel shrugs one shoulder, otherwise remaining still. “Don’t think you want things gettin’ tough for you, mister,” Head Goon continues when the silence between them starts to stretch out.

“Tell your chicken boss that if he’s got an issue with me or someone inside my bar to come and take care of it himself,” Castiel says, looking bored with this entire situation and the little over half dozen sulfur-scented mobsters threatening to shoot up his bar.

“You don’t want this kind of heat, bub. Just move aside and my buddies and I will gladly leave you and your little bar here alone.” Castiel raises an eyebrow, unimpressed. Head Goon frowns then, like he’s trying to figure out where he’s seen Castiel before. “Wait a minute, I’ve hearda you. Ain’t you that queer fathead that tried to frighten the boss aways back?”

Now Castiel actually is bored with this situation. “My reputation precedes me,” he replies dryly. “Now that you’ve determined who I am, can I assume you’ve resolved to never come within ten feet of my bar ever again and skip?” Head Goon laughs and steps even closer to the bar, coming just within arm’s reach of Castiel. Castiel sighs before disarming Head Goon and pressing his knife up against Head Goon’s neck, effectively shutting the fathead up. “I’d hate for my assumption to be incorrect,” Castiel says as if he’s discussing the weather. Head Goon nods minutely, trying not to press the knife even further into the sensitive skin of his neck. “Good. Now scram.”

As soon as Castiel takes the knife off of Head Goon’s neck, he’s treated to the sight of Head Goon scrambling off into the fading sunlight, unarmed, along with the other half dozen sulfur fuckers who acted as his backup. Castiel lets out a breath then, his shoulders slumping from where he’d had them up to his ears. A hand falls on his shoulder, and Castiel spins around, his knife against Sam’s throat before he realizes that it’s just Sam. “I was gonna say good job but I think I should offer you a drink instead,” Sam says with a slight laugh, his hands up in the universal gesture for surrender.

Castiel sighs again, bringing the knife down and running his free hand down his face. “My apologies, Sam. It’s been a very long time since I’ve had to do something like that.” He turns back to the door, taking up the doorstop and closing it before turning the sign from OPEN to CLOSED. “Any idea on who our mystery guest is?” Castiel asks as the two of them make their way back over to the bar, Castiel noting the lack of random unconscious person in the bar’s main room.

Sam smiles fondly, and Castiel has a sneaking suspicion that his earlier glimpse had been correct. “Yeah. My brother, the only guy I know dumb enough to be wanted by local mobsters within twenty-four hours of being in town,” Sam explains, and Castiel works very hard on putting on a surprised/interested expression. It doesn’t seem to be necessary though, as Sam doesn’t look at Castiel and instead focuses on pouring both of them two fingers of whiskey. “Any chance he could stay here tonight? I put him in the bedroom in the back, just cause I didn’t want to chance any of those mobsters getting in.”

 _There goes any chance of me sleeping in my own bed tonight_ , Castiel thinks forlornly. “I doubt he’ll be getting up anytime soon, what with how hard you punched him,” he says aloud, accepting the drink with a slight nod of his head. “Excellent punch, by the way.”

Sam flushes a little under the praise, which is ridiculous because he’s twenty-nine years old. “Thanks. Dean actually taught me how to do that, back when we were kids. Kinda ironic that I used it on him, huh?” Castiel hums in agreement before sipping his whiskey. “Hey, Castiel,” Sam says, once silence begins to fill the space between them. “About that guy, that other Dean you knew - what made him so memorable?”

Castiel sips his whiskey again as he considers his options: he could tell the younger Winchester the truth, or he could make up some sort of story. Given who’s currently occupying Castiel’s bedroom, Castiel decides that the truth is probably the better option in this situation. “He pulled me out of a very dark place and set me on a better path, a path where I was free to make my own choices.” Castiel smiles when he catches the confused look on Sam’s face. “I used to be in a mob. It’s not a time in my life which I look upon with any particular fondness.” He sits up a little straighter, sensing a need for a change in topics. “Will you be staying to look over your brother?”

“No,” Sam answers with what Castiel thinks is another laugh, like Sam can’t imagine what would happen if he _did_ stay over to watch his brother. “I trust you, Castiel, plus you just put your own life on the line to keep some mobsters from filling my brother with holes. I’m gonna head home so that I can make it back here sorta early tomorrow.” Castiel nods, acknowledging Sam’s reasoning and implied planned meeting for the next day. “You gonna be okay staying here in the bar overnight?” Sam looks skeptical when Castiel nods again, but he doesn’t question it. “Alright then. I’ll see ya tomorrow. Night, Castiel.”

“Good night, Sam,” Castiel says, and Sam leaves, letting the bar’s front door swing shut with a quiet chime of the overhead bell. Castiel finishes off his whiskey before he stands and locks up the bar, front door then the back. When Castiel comes back to the bar, he pours himself another couple of fingers of whiskey. “What the hell are you doing, Novak?”  Sighing again, Castiel glances towards the back, where his bedroom lies beyond a short hallway. He turns back to his whiskey, determined to push the thought of any Winchester out of his mind.

Of course, the Universe has other plans.

“ _You must remember this: a kiss is just a kiss, a sigh is just a sigh_ ,” a voice croons from the direction of Castiel’s bedroom, and Castiel lets himself have this sappy moment before everything goes to shit. The singer isn’t bad, though it’s obvious he doesn’t spend a lot of time honing his singing voice. His voice is soft, like he’s waiting for Castiel to reprimand him, and he trails off into a quiet hum after the first two lines.

Castiel huffs quietly before picking up where his visitor left off. “ _The fundamental things apply as time goes by_.” He shakes his head though, before downing the rest of his whiskey in one go. “Knew I should’ve gone under an alias,” he mutters just loud enough for the only other person in the room to hear him.

“Don’t suppose it would’ve made much of a difference,” is the reply he gets. “After all, you were pretty clear in your demand for me to just leave you the fuck alone.” Castiel lets out a sharp laugh before he can stop himself. “Have to admit, never pegged you as the bartending type.”

If Castiel stands a little straighter, there’s only one other person in the room to see it. “There are quite a few things I believe you never _pegged_ me for.” Finally, Castiel turns around to face his unwelcome visitor. “You’re a son of a bitch, Dean Winchester, you know that?”

The laugh that follows Castiel’s comment almost sounds real, and it warms Castiel to the core, even if he doesn’t want to admit it. “It’s good to see you too, Cas,” Dean Winchester replies with a smile.


	2. as if it were the last time

Castiel feels more than a little justified in crossing the bar just to slug Dean Winchester. “That’s for sleeping in my bed uninvited,” Castiel says, shaking his hand out while Dean brings a hand to gingerly press against his cheek where Castiel’s fist had met his face.

Dean scoffs, wiping the corner of his mouth to see if he was bleeding, turning his eyes back to Castiel when he sees he isn’t. “‘Spose it’s too much for me to ask for a hello?” He stalks away from Castiel and towards the bar, pouring himself whiskey using Castiel’s glass.

“Eight years, Winchester. Eight goddamn years without hearing a single word about whether you’re alive or dead while I’m hiding from one of the biggest mobs in the country. Talk about love ‘em and leave ‘em,” Castiel adds in a huff under his breath.

“Hey, _you’re_ the one who told me to stay away, remember? I went looking for you, and I found you, and you told me to get the hell out.” Dean points at Castiel with his free hand, the other swinging the glass of whiskey around. “Hate to break it to ya, baby, but this separation? All on you.”

Castiel glares at Dean. “If you’re following my orders, what’re you doing here then? Don’t tell me that the great P.I. Dean Winchester has actually failed to do the research on the town where his brother’s been living for two years. You had to have known that I live here too.”

Dean returns the glare with the same amount of force. “For your information, I’m getting married. Thought it might be nice to actually let the best man meet the bride before the wedding. Wasn’t like I was expecting to spend a lot of time in bars while I was here,” he snaps, turning away for a moment. When he looks back at Castiel, he’s surprised to see all of the fight drained out of the other man. The bottom of Dean’s stomach drops out, and he thinks Castiel might punch him again.

“Congratulations.” Dean blinks in the face of Castiel’s sudden monotone. “Would you like me to pour the groom a shot for his nerves so he can get the hell out of my bar?” Castiel crosses back behind the bar, keeping his eyes averted while Dean watches him blankly. “I’m afraid that if the groom’s looking for a kiss for good luck, he’s a little too late to be asking for it.”

The fist that falls on the counter startles Castiel enough for him to actually look up at Dean. “Dammit, Cas, what did I _do_?” Dean looks tired, the bags under his eyes more pronounced and the open expression on his face making him look ten years younger. Castiel wants to reach out a hand, try to wipe some of that look away, but he knows he isn’t allowed, not anymore anyway.

Instead Castiel looks away, pouring himself a drink in a clean glass. He does his best to ignore the look on Dean’s face while he does, running through his options in his head. “Bedroom’s yours if you want to stay here. Sam wasn’t expecting you to be able to make it back to the hotel room I’m assuming you have, so he’s coming over in the morning to check on you.”

Dean shakes his head before downing the rest of his drink. “No, I think I’ll just go.” He glances at Castiel as he tugs on his jacket like it needs to be readjusted. “You gonna tell Sam I went back to my hotel when he drops by tomorrow morning?”

Castiel hates the way he wants to be _fond_ about the way Dean asks that, like this isn’t actually the first time they’ve seen each other in almost eight years and that there isn’t a whole maelstrom of shit floating between them that really needs to be discussed or, as is the more likely option, further ignored. “Yes, I’ll inform your brother that you left for your hotel after I did my best to give you a black eye,” he says, walking out from behind the bar and towards the front door to unlock it.

Dean laughs as he follows Castiel to the door, and Castiel doesn’t stop himself from shooting Dean a curious look. “I forgot that you’ve actually got a killer sense of humor.” He steps around Castiel to the open doorway, his mouth open like there’s something on the tip of his tongue that he needs to say. Dean shakes his head after a moment, sending Castiel a tired smile. “I’ve got the feeling that we’re gonna end up talking about everything.” He bites his lip before settling on,  “Night, Cas.”

“Good night, Dean,” Castiel replies, and Dean nods before walking away. Leaning against the doorframe, Castiel watches Dean for a few seconds before moving back inside to lock the front door again. He’s gonna need more than a few drinks if Dean Winchester’s back in his life.

* * *

Sam pounds a fist against the door to Castiel’s bar, worry growing every second that Castiel doesn’t open up. He’s heard Castiel say how he likes to be up early, how the bar owner doesn’t get much in the way of sleep anyway, so it’s unlike Castiel to be taking so long to answer his front door - that is, assuming he stayed in his bar last night. Which Sam does. Assume, that is. Which is why he’s worrying.

What if those mobsters came back and Castiel couldn’t handle them? What if Dean did something stupid that made Castiel shoot him? Honestly, the second option seems more viable than the first, but Sam still worries about mobsters that Castiel managed to send away with nothing more than a few choice words and a well-delivered knife to the neck. Come to think of it, maybe Sam shouldn’t be worried about the mobsters. Maybe he should just be worried that Dean did something stupid.

It feels like an eternity has passed by the time Sam hears the key turn in the door’s lock and the door opens to reveal Castiel’s tired and, if Sam didn’t know any better, hungover face. “Castiel?” Sam asks, and Castiel blinks slowly, confirming Sam’s suspicion of a hangover. “What the hell happened to you?” He steps forward, pushing Castiel back slightly in order to make it into the bar.

A few more seconds pass before it looks like Castiel’s brain has fully processed Sam’s question and come up with a viable answer. He squints up at Sam, even though there’s more sunlight behind him than there is in front of him. “I had an open bottle of whiskey or two,” he says, turning away from Sam to walk back to the bar proper.

Sam just stands there in the middle of the seating area, watching Castiel walk away. “And?” He’s confused. He’s never known Castiel to get drunk before, much less suffer from a hangover. Dean must’ve really been a handful if Castiel opened more than one bottle of whiskey to deal with him.

“And I drank it,” Castiel replies, immediately pressing the heel of his palm against his temple as if he could fight off the sound of his own raised voice. He wanders around the bartop to collapse behind it, effectively hiding him from Sam’s view. Going by the sound, Sam guesses that Castiel has some sort of bedspread set up. He follows Castiel’s path, just reaching the gap between the wall and the bartop when Castiel mutters something. At no reply from Sam, Castiel rolls over onto his back and repeats himself. “Your brother is a menace to society.”

Sam snorts in response, leaning against the bartop. “Yeah, no surprise it only took your a few hours to figure that one out.” He glances towards the back hallway where he found the bedroom and laid his brother down the evening before. “Where is Dean, anyway?”

Castiel huffs out what Sam thinks is a laugh, but the look on Castiel’s face is anything but amused. “Your brother went back to his hotel yesterday, once I did my best to give him a black eye. If you’d excuse me, Sam,” he continues, ignoring the way Sam’s jaw drops open in favor of grabbing one of the blankets and pulling it over his head.

“What? Why’d you try to give him a black eye? He didn’t anything asshole-ish, did he?” Sam squats down in order to shake Castiel’s leg. “Hey, Castiel. Castiel,” he tries again when the only thing he gets in response is a groan. “Castiel, why did you try to give my brother a black eye?”

Castiel throws the blanket off of himself and sits up, startling Sam enough that he nearly falls back on his ass. “Why did I try to give Dean a black eye? Because I’m angry that he has even an inkling of the notion that he’s allowed to bother the mobsters in the town where I live and then come in here trying to woo me with that damn song after - !” He shuts his mouth with a click, laying back down and grabbing the blanket to hide beneath it again, like he’s a child and not a man in his mid-30’s.

Sam blinks. And then he blinks again. And then, just for the hell of it, he blinks a third time while trying to process the words that just came out of Castiel’s mouth. Finally, “He tried to woo you?”

“Unsuccessfully, if I might add,” Castiel answers, just slightly muffled by the blanket over his face.

If Sam blinks again, he thinks some of what he’s just heard might start to make a little sense. Miraculously, it seems to work as some of the pieces begin to come together. “Castiel,” Sam says slowly, “how likely is it that the Dean you mentioned you knew a while back and my brother are the same person?”

Castiel’s silence is an answer in and of itself.

“Holy shit,” Sam says faintly, and he thinks he sees Castiel nod from under the blanket. He runs hand over his face while he tries to reconcile the fact that Castiel’s probably known who he was in relation to Dean the entire time they’d known each other, and probably for a while before Sam had even heard of Castiel. “Y’know what, why don’t you stay there, under your blanket, until your hangover wears off. I’m gonna go find Dean and possible beat some answers about what the hell went on between you two out of him.” Castiel waves a hand, and Sam takes that as his cue to get the hell out of there so he can figure out what just happened to his life.

* * *

For the second time in less than an hour, Sam finds himself pounding his fist on a door. Only this one happens to belong to his brother, if only temporarily.

He pauses long enough to press his ear to the door to make sure that he actually heard Dean groan his acknowledgement to Sam’s insistent knocking before resuming his attempt to make a dent in the door. “I know you’re awake, Dean, open up.”

It only takes a few more seconds before the hotel room door swings open, revealing a very tired Dean Winchester. If Sam had to guess, he’d say his brother didn’t get any sleep since he left Castiel’s bar last night. Sam’s plan had been to storm into Dean’s room and demand some answers about what the deal was between his brother and Castiel, but just seeing his brother changes that. “I take it Cas sent you,” Dean says drily, turning back to his room. He leaves the door open, though, so Sam takes it as an invitation to come inside.

Sam shakes his head, closing the door behind him. “I went to look for you at Castiel’s bar but you’d already left.” He furrowed his eyebrows with a frown, something Dean’d said catching his attention. “You call him Cas?”

Dean raises an eyebrow at Sam over his shoulder. “Yeah? What do you call him?”

“Castiel,” Sam says, emphasizing the last two syllables. “Never got the impression that he’s the type to go by a nickname.”

“Oh. Whoops,” Dean says by way of a reply, picking up what looks to be a glass of whiskey if the bottle it’d been sitting next to was any indication. He takes a sip while Sam thinks of something, anything, to say, preferably something along the lines of “What’s going on?”

Instead, Sam runs a critical eye over the two pieces of luggage Dean brought with him - one suitcase and one duffel bag. “You couldn’t have brought more stuff with you? You’re getting married, Dean.”

Dean waves his free hand dismissively. “It’s all I felt like bringing.” He leans his hip against the dresser, his face carefully blank. “Besides, I thought you weren’t here to criticize my packing choices.”

“No, it’s your other life choices I’m here for,” Sam replies dryly. Dean rolls his eyes like Sam expects him to, and for a moment, it’s like they're not actually about to discuss something Sam didn’t even know happened to his brother until about an hour ago. “You and Castiel, huh?”

His brother glances at him, most of his focus actually on the whiskey in his hand. “You’re really gonna push this, aren’t you?” Sam nods, and Dean lets out a deep sigh, which is all Sam needs to hear to know that he’s won. “C’mon, Sammy, it was eight years ago. What about it could be so interesting?”

Sam frowns, ignoring the obvious use of his childhood nickname as a ploy to get him to leave the subject alone. “Castiel told me that the Dean he knew pulled him out of the mob and set him on a path where he could do what he wanted, of his own free will.” He raises his eyebrows at Dean to convey a silent “Seriously?” “I think that’s more than enough to get me interested.”

“Fine,” Dean says before finishing his whiskey. “But it’s a long story, even without the parts you aren’t old enough to hear yet,” he adds teasingly, moving to refill his glass.

Sam huffs and rolls his eyes - he knows that Dean’s avoiding telling him. “That stopped working on me when I was thirteen, Dean,” Sam replies. “Tell me what happened between you and Castiel eight years ago.”

When Dean looks over at Sam again, it’s to the discovery that his brother is using his patented Puppy Dog Eyes™. “Get settled in. It’s gonna be a while before we go anywhere.” Sam takes the opportunity to sit on the bed, while Dean sits in the room’s only chair. “Here goes nothing,” he mutters to himself, though Sam still catches it.

“I was working this job for a client who said his daughter was being hunted by the mob. Never caught her name, he’d guessed she’d changed it anyway. So, I went looking around where the client said his daughter’d been working before she went off the map - some place called Pontiac in Illinois.”

* * *

_**Eight years earlier** _

Dean’s less concerned with the hole in his arm than he is with trying to _not_ get another hole somewhere more important, like his gut or his head. If he was paying more attention, Dean might think that the way his coat’s flying out behind him while he runs is pretty damn cool. As it is, Dean’s just trying not to get shot again. The raindrops falling onto his hat and overcoat aren’t doing a lot to help Dean’s mood, though he’s betting that the rain’s actually helping him keep from getting shot again.

He ducks into an alleyway he’d almost run past, trying to breathe as quietly as possible so the assholes shooting at him will run right past him in his darkish alleyway.

Surprisingly, they do, their footsteps loud against the street as they continue down the path Dean’d been pulling out of his ass. It gives Dean an opportunity to sigh and lean against the alley wall, wincing as he jostles the arm with the hole in it. He twists around to bring his arm towards the light, trying to get a look at the damage. At the sight of it, Dean lets out a heavy sigh. It’s not actually a hole, but it’s definitely gonna need a few stitches. “Fuck.”

“Well, that’s rather forward of you, considering we’ve just met,” a deep voice further down the alleyway says, immediately putting Dean on alert, the P.I. pulling out his gun with his uninjured arm. “Also rather presumptuous, thinking that I’d be willing to take you up on such an offer.” The owner of the voice keeps walking towards Dean, only stopping when the barest hint of light from the nearby streetlamp hits his face just right.

If Dean weren’t so concerned that this mystery man might be trying to kill him, Dean might be tempted to ask the man out for a drink, dark hair beneath the fedora and a slightly stubbled jawline. Ignoring the slightly ill-fitting suit, Dean wouldn’t mind being seen out in public with the man. Of course, he _is_ still holding a gun in the man’s direction, so maybe not. “Oh yeah? What makes you think I was asking you?”

The man actually laughs, the fucker. “Perhaps you would prefer it if I killed you, instead of offering to assist you in the treatment of you wound.”

Dean blinks. What the actual fuck. “Did you just imply that you were sent to kill me?”

“Oh, no,” the man replies. “I’m stating it as a fact.”

 _Oh, well fuck,_ Dean thinks, staring at the other man. If this guy’d been sent to kill him, then Dean had no doubts that the other man could kill him before he even realized what was going on. So, in one of the stupidest decisions of his life, Dean puts his gun back into its holster. “In that case, I think I’ll take your offer for help.”

**Notes for the Chapter:**

> thanks to everyone who commented and left kudos! two weeks - not my best update time, but still pretty good. i'd actually planned to get this done a week ago, but motivation was not with me that day.  
> chapter three is in progress, i promise! (maybe, if anyone cares to know)  
> 


	3. we'll always have pontiac

**Notes for the Chapter:**

> sorry! three weeks is a long time to wait for a shitty chapter like this. i meant to finish this last week, but i'm working this summer, and that equals zero free time during the day for me, and waking up at 6 every morning, so late night writing isn't an option. but it's here now, and i hope that means something  
> also, i apologize in advance for the number of breaks i have in this  
> thanks again to everyone who's commented or left kudos!

“Are you trying to tell me that the first thing Castiel ever said to you was a sexual play on words?”

Dean glances at his brother, stopping short at Sam’s dropped-jaw expression. “What?”

Sam shakes his head after a moment. “Sorry, trying to process that One, Castiel hit on you in the most obvious way possible, and Two, you decided to accept the help of a man who admitted he was there to kill you.” He shakes his head again in disbelief. “What were you thinking, Dean?”

Dean purses his lips together before answering Sam’s question. “I was thinking that you weren’t back at the office to give me a hand with the stitches.” Sam’s amused expression drops away then, a wave of guilt crashing over him as the time frame fell into place.

College. Eight years ago, Sam’d been off at college studying to get into Stanford to become the lawyer he is today. That included leaving Dean to tend to the family business by himself. On the bright side, that means that Sam’s technically the reason that Castiel and Dean met in the first place.

Sam shakes his head, ignoring the guilt for not being there and the slight pride at being the reason his brother and Castiel met. “Anyway, you went with him, despite the fact that he could’ve killed you at any time and was probably going to. What then?”

Dean gives Sam a weird look. “Then what? He sewed up my arm, decided to let me live, and let me go my merry way?”

His brother rolls his eyes. “How’d you find out what his name was? I mean, I assume it came up in the course of your investigation, but something tells me that’s not right.” Sam sees the way Dean hesitates, and he really wants to dig in and push for Dean to give him all of the answers. Then Sam thinks of Castiel and the way he automatically shut himself up when he was about to mention whatever it was that happened between him and Dean, and he doesn’t.

What Sam would give to be in Dean’s head right now.

* * *

Dean’s really glad Sam’s not in his head, cause his head is doing some very not appropriate things right now - namely, getting stuck on the huge sexual innuendo Castiel laid on him when they met and all the mental images that went with it.

He manages to clear his throat in order to answer Sam’s question. “He told me.”

Sam’s eyebrows shoot up his forehead. “He _told_ you? Just like that? Did you even have to ask?” Dean shrugs in a _eh, kinda_ way and silently prays that Sam doesn’t realize that Dean’s blushing more than just a little. “What’d he say?”

_“My name is Castiel, since you were wondering.”_

_“Castiel? What kind of a name is Castiel?”_

_A smirk, a flash of baby blues. “One I’d like to hear you scream in bed, Mister Winchester.”_

Dean shifts in his seat, trying to not think about Castiel in bed with his brother right there. “You know how he is, vague and cryptic. His name was the first straight answer I got out of him.”

Sam shakes his head. “I still can’t get over the fact that he propositioned you right off the bat. Now I’m starting to get why he said you were trying to woo him last night.”

Dean’s a split second away from asking Sam exactly what Castiel said when someone knocks on the door. A quick glance at his watch confirms his suspicions, and Dean doesn’t bother with any of Sam’s questions as he stands to answer the door.

He does however look as smug as possible when he opens the door to reveal his fiancée, Lisa Braeden.

“Dean!” She pulls him into a hug, one of her arms reaching up and around his neck. “How was the trip?” Lisa steps back then, studying Dean’s face and frowning. “You ran into some trouble, didn’t you?” He opens his mouth to respond but she doesn’t let him, catching sight of Sam. “Are you inviting men to sleep with you without me again, Dean?”

Sam coughs then, hiding a wide smile behind his hand at Dean’s panicked and slightly embarrassed expression. “Sam Winchester, ma’am,” he says, standing and stepping forward, his other hand out towards Lisa.

Lisa smiles sweetly up at him. “Oh, I know. I just like making fun of Dean.” She shakes his hand while Sam raises an eyebrow at his brother. “Lisa Braeden. I’ve heard wonderful things about you, Sam, mostly in between the lines of the stories that Dean tells. He’s very proud of you.” Sam looks at Dean, trying to either prove or disprove what Lisa’s saying, but Dean’s already turned away from him to do something else.

He turns back to Lisa, smiling again. “Well, thanks for that, and I’m glad that at least someone else thinks Dean needs to loosen up sometimes.” Both of them ignore Dean’s affronted “hey!” “I know the entire point of you coming here was for us to meet, but I think you and Dean both have some things to be working on for the wedding,” Sam continues.

Dean finally turns back around to Sam, catching on to where Sam’s thoughts are headed. Lisa, of course, is completely oblivious. “Oh no, Sam, stay for a while. I’m pretty sure that if the two of us work together, we’ll be able to convince Dean to buy us lunch.” Her fiancé looks more relieved than he should be at the prospect of Lisa and Sam working against him and him having to pay for lunch, but if it keeps Sam from asking Castiel’s side of the story for a little bit longer, he’ll take it.

Of course, Sam’s following Dean’s train of thought, and, while the prospect of getting to know Lisa better is exciting, he’s still curious about what happened between his brother and Castiel. Maybe he’ll manage to talk himself away after lunch, give Castiel time to get over his hangover. “Sure,” Sam says, and Lisa lights up even more. “I’d be happy to have lunch with you guys, if Dean’s paying.”

* * *

Castiel’s better than he was this morning, when he finally gets around to opening the bar around three, but only marginally so. It’s been a long time since he’s drunk enough to get a hangover, and it’s been his curse in life that his hangovers always stick around for a long time.

Fortunately and unfortunately, today seems to be an easy one, just over a dozen people having stopped by by the time seven o’clock rolls around. Castiel’s thinking about closing up early when Sam walks through his door, an easy smile on his face.

“I should’ve known that a hangover wouldn't have kept you from opening up today,” Sam says as he approaches the bar, sliding onto his regular stool. Castiel shrugs, and tries to avoid eye contact. “I asked Dean about what happened between the two of you, but he didn’t get very far before his fiancée showed up.”

Castiel glances up at Sam. “Oh? Anything particularly interesting to give you some insight into the past?”

Sam plays along, adopting a look of casual indifference. “The usual, Dean getting shot, some guy apparently sent to kill him helping his sew his arm shut. Nothing out of the ordinary.” Castiel doesn’t stop himself from rolling his eyes. “Though it was kinda interesting how the guy hit on Dean within about five seconds of meeting him.” If Castiel had been drinking anything, he would’ve choked on it. “Funny, doesn’t usually happen when Dean’s just been shot.”

Castiel very determinedly says nothing about the sly look on Sam’s face, ignoring the coloring of his cheeks at Sam’s innuendo. In all honesty, he’s forgotten what he first said to Dean all those years ago, the words lost in a rush of adrenaline. Past that, though, everything seems to stay in startling clarity. “I suppose you want to know what happened after I left your brother in a shitty hotel room to sleep off the adrenaline once I knew he wasn’t about to bleed out.”

And Sam’s head perks up in the exact same way it had when Castiel admitted to knowing a Dean in the first place. Castiel grimaces as he comes to the realization that Dean probably didn’t go into depth about Castiel helping him. It didn’t seem like Sam needed details about sewing his brother shut after a bullet wound. “I would’ve asked more,” Sam says, obviously enjoying Castiel’s discomfort at the moment, “but Dean didn’t seem too keen to talk about you with Lisa around.”

“Very well then,” Castiel says, mentally noting that Dean was probably actually going to kill him this time, since their versions of events might not line up exactly. “Your brother’s reputation wasn’t exactly unknown to us, the Novak mob, and his stubbornness was only matched by his desire to do good. I thought that if someone stepped in and warned him off directly, he might be willing to back off of the case. Needless to say, I wasn’t very successful.”

* * *

**_Eight years earlier_ **

To say Dean Winchester’s office is a nice place would be a little too generous. Yes, it has decent furniture and a non-garish color splashed on the walls, but it’s still only a temporary place, one that Castiel knows Dean’s renting out until his business with the Novak mob is concluded.

Or until someone warns him away before he ends up shot again, as Castiel is hoping to do, hence his presence at the temporary office.

But Dean’s not there at the moment, so Castiel takes the opportunity to snoop around the tiny space, consisting of not much more than a desk, a chair, a desk lamp, and what appears to be a bedroll spread out on the floor between the desk and the room’s only window. If Dean is truly that low on funds, Castiel wonders why he rented the space to begin with, instead of just setting up shop in a hotel room. The sleeping accommodations would’ve at least been slightly better.

Castiel’s just picked up what looks to be the only book in the room, sitting on the desk beside a case file, when he hears the hammer of a pistol being pulled back, signalling Dean’s return. “I suppose I could ask you what you’re doing here, but I think I’m more likely to shoot you than ask any questions.” This, Castiel supposes, is what he gets for being curious and impatient. He slowly turns around, aware that Dean is completely willing to shoot him. “Castiel?”

The surprise on Dean’s face leads Castiel to smile a little. “Hello, Mister Winchester. My apologies for entering your office unattended, but my curiosity persisted.” Dean huffs a little and clicks the hammer back, holstering it as Castiel brings his hands down.

“What brings you around here?” Now that Castiel isn’t focused on the gun, he sees the bag of groceries wrapped in one of Dean’s arms. Despite his obvious suspicion, Dean moves fairly easily around the office, even with Castiel in the room.

Castiel gets so caught up in the domesticity of the situation, Dean pulling groceries from the bag, that he only remembers to answer Dean’s question when the P.I. glances up at him. “I came to see how you were doing,” he says, though it sounds weak even to his ears.

Dean snorts, pausing in removing food. “Bullshit. You were sent to kill me, remember? Don’t think would-be killers keep tabs on their very alive targets.” He turns to lean against the desk, his arms folded across his chest as he looks at Castiel. “So, what’re you doing here? And if you say you’re just here to see me, I will shoot you.”

Castiel hesitates for a moment before speaking again. “I came to see if you could be persuaded from continuing to pursue the case that brought you to Pontiac in the first place.” He doesn’t know what the strange look on Dean’s face means, or why he wants to warn Dean away (other than the fact that he is incredibly attractive). Either way, Castiel keeps talking. “The Novaks are not easily thrown off, and I’d guess that you were very lucky I arrived when I did otherwise you would’ve gotten off with more than just a bullet wound in your arm.”

The hum Dean lets out could either be agreement or acknowledgement, but Castiel doesn’t actually know which it is. “Sounds like you’ve got some experience.”

“I don’t suppose there’s any way I could convince you I’m not involved when I was the one sent to kill you,” Castiel says dryly, breaking up the growing tension in the room. He stands his ground, even as his staring contest with Dean seems to be getting out of hand. “I won’t lie, I am associated with the Novaks, and have had experience with their head, Michael Novak. He isn’t one to take no for an answer, especially if it’s something he’s ordered to be done.”

Dean lets out a quiet “huh,” and Castiel suddenly worries that he’s said too much, that Dean will figure out his real connection to Michael just by that comment. Then Dean’s expression shifts into a calculatedly lazy smile, and Castiel relaxes a little. “Sorry, Cas, no can do. Client paid me to see the end of this case, whether it involves a corpse or a breathing body.”

It’s not much, especially when Castiel was hoping to get Dean out of harm’s way, but now he’s got some idea of what Dean’s investigating. “I’ve got the feeling your honor’s gotten you into your fair share of trouble before.” Dean shrugs, but the slightly larger and more genuine smile on his face betrays him. “Well, I suppose that means we’ll run into each other again before your time in Pontiac is through.”

Dean stands then, obviously ready to show Castiel out so he can get back to work. It’s more than obvious that Dean doesn’t trust Castiel, and Castiel isn’t particularly inclined to offer his help in his investigation. He might’ve said that they’ll see each other again, but that doesn’t make it true. “I’ll see you around then, Cas.”

Castiel raises an eyebrow, the shortened version of his name startling outside of family use. “Cas?”

Dean looks caught, and his cheeks color slightly. “Slip of the tongue.”

Castiel shrugs, smirking a little. “Not quite the tongue slip I was looking for,” he says with a wink before he’s out the door, pleased with himself at the subtle nature of his innuendo. Even if he hasn’t managed to get Dean to leave the case alone, at least he’s finding a way to keep the attractive man within arm’s reach.

* * *

Castiel watches as Sam almost chokes on his drink, finally catching onto Castiel’s innuendo. “I’m suddenly so glad Dean didn’t tell me everything about you sewing him up if every other thing you said was as bad at that,” Sam says once he’s cleared his windpipe. When Sam looks at Castiel, the bartender just grins widely, zero shame about his behavior. “Oh, man, gross. That’s my brother you’re talking about.”

“It doesn’t mean I can’t appreciate his physical attributes.” Castiel pauses a moment to give Sam a significant look. “Or yours for that matter.” When Sam almost chokes again, Castiel laughs, hiding his mouth behind his own glass.

“Not funny,” Sam rasps when he’s gotten the majority of the whiskey out of his windpipe. Castiel’s still grinning when he slides a glass of water across to Sam, the younger Winchester attempting to give him a death glare. “Hell if I know why Dean seems to like you so much.”

Castiel’s fairly certain Sam means it as a joke, but it still makes him take the glass away before he ends up choking on whiskey or spitting it everywhere. Once he’s certain it’s no longer a hazard, he looks at Sam, who looks as smug as the cat who just got the canary. _Damn_ , Castiel thought. While Castiel’s never thought that Sam was dumb by any means, he had hoped to keep Sam thinking that he was only attracted to his brother physically. Sam might not think that there’s anything wrong with bringing emotions into it, and Castiel knows that they’re going to show up, but it doesn’t mean that it’s not gonna hurt like hell.

**Notes for the Chapter:**

> chapter 4 may or may not be in progress. it's early yet, if two-thirty in the afternoon can be called early, so i might get some more written today


	4. his least vulnerable spot

**Notes for the Chapter:**

> whoops, three and a half weeks later, here's a new chapter. truth is, i probably should've had this finished a week and a half ago, but i never got around to it/i never got the time  
> anyway, here's the next bit, with a new addition to the cast

Pleased that he seems to have gotten one up on Castiel, Sam’s grin stays firm as he leans onto the bar again, his curiosity still piqued despite his jabs at the bartender. “So, what happened next? I mean, obviously Dean found out something else about you, ‘cause there’s no way he’d leave it alone, what with you finding out where he’d set up shop.”

Safe for the moment from Sam’s observant nature, Castiel takes the opportunity to finish his whiskey, pouring himself more as he replies. “If only you’d been there eight years ago, you might’ve warned me away,” he says wryly. “Being the man he is, your brother managed to find out the truth of the nature of my relationship with the Novak mob.”

Sam narrows his eyes. “But there’s more to it. Dean already knew you were connected to the Novaks, you said so yourself.”

Castiel sighs, and even after all this time of knowing Sam, it still surprises Castiel how alike he and Dean are. Sam’s leaned forward again, waiting for Castiel to fess up, give up the truth of his relationship of the Novaks. And, even though it’s been eight years of hiding from Michael, Castiel’s still hesitant to let anyone know the truth, even though he knows Sam can take care of himself. “That, not only am I a Novak, but I am one of the members of the main family. My older brother, Michael, is the current head of the mob.”

Unfortunately, Sam’s silence gives Castiel the perfect opportunity to continue with how Dean decided to confront Castiel about this development.

* * *

**_Eight years earlier_ **

The presence of a warm body behind him isn’t exactly a new experience to Castiel, especially given the club’s seedy atmosphere and Castiel’s not-so-quiet reputation with the fellas in these parts. Still, Castiel isn’t expecting company, much less anyone as fit as this visitor seems to be.

“Mister Novak,” a low voice murmurs into his ear, and Castiel suddenly finds himself cataloguing where every other member of the mob is in the club.

Raphael, Michael’s right hand, is across the room and in deep conversation with someone Castiel knows he should recognize but doesn’t because Dean’s breath against his neck is incredibly distracting. He doesn’t see anyone else of consequence, so Castiel turns his head towards Dean. “What are you doing here,” he hisses at the P.I. “Do you have any idea how much danger you’re in right now?”

Castiel feels more than sees Dean’s shrug, which says something about how close they’re standing. “I dunno, I’ve got a pretty capable bodyguard and I’m handy with a gun if it comes down to a shootout.”

“The last time I saw you in a shootout I had to help you escape,” Castiel replies, keeping an eye on Raphael, who looks more and more disinterested with his conversation by the moment. “So, again, what are you doing here?”

Dean shifts on his feet, and Castiel assumes he has a drink of some kind judging by the movement of Dean’s arm. “Thought I’d drop in, see how the youngest Novak was doing. You _are_ the youngest Novak, right? My sources weren’t sure whether it was you or one of your cousins, Anna, I think it was.” He throws his head to the side in a throwaway move. “Pretty girl from what I can tell in the few photos I got my hands on.” Dean takes another drink, and Castiel takes those precious few seconds to wish he’d actually done his job and killed Dean when he had the chance.

“Dean, this isn’t funny.” Castiel glances away from Raphael for long enough to shoot Dean a quick glare. “There are multiple high ranking members of the Novaks here, and almost all of them are aware of the price Michael has placed on your head.” When he looks back at Raphael, he doesn’t like what he sees.

It’s with no small amount of concern that Castiel sees Raphael turning his head in their direction from across the club. It’ll be easy for Raphael to recognize Castiel, and take only a few moments more for Raphael to identify Dean as his companion.

Castiel grabs Dean by the arm and pulls him towards the back, ignoring Dean’s questions as to what he was doing. When Castiel risks glancing back, he sees Raphael following them. “Dammit,” he mutters, and Dean turns around to look, but Castiel pulls on his arm to prevent that. “Don’t turn around. We’re being followed by Michael’s right hand man.”

Of course, Dean turns his head around to get a look, _again_ , but Castiel tugs on his arm sharply. It’s enough to keep Dean looking at Castiel and not at Raphael. “Ow! What was that for?” Dean has to extend his stride to keep up with Castiel, even though he’s the taller of the two, glaring at the other man.

“Would you _like_ Michael’s right hand man to know that you’re still alive and currently in my presence?” Dean shuts his mouth with a click, audible even with the music playing loud enough to keep people from talking, and Castiel has to bite his lip to keep from smirking. There are other ways to shut Dean up, but none of them seem appropriate at the moment.

That thought almost stops Castiel in his tracks. One of them actually is appropriate given the situation, and just distracting enough that it might get Raphael to leave them alone. Castiel takes in the even lower lighting in the back of the club, and sincerely hopes that his actions aren’t about to earn him a punch in the face. It won’t necessarily do much, given Castiel’s quick healing ability, but it’ll certain hurt like a bitch.

Castiel pulls Dean into a semi-private alcove, one of the many he knows the club has. Dean’s apparently learned to just do as Castiel tells him for the moment, given that his life, and Castiel’s professional reputation, are on the line. But his P.I. nature comes back to him with an obvious confused expression when, after letting one of the privacy curtains close, Castiel throws himself against the wall facing the alcove’s entrance, making it look like Dean’s bracketing Castiel in. “What?”

There’s not much time for an explanation, so Castiel doesn’t offer one. “Sorry,” he says quickly, before sliding a hand along Dean’s jaw and pulling him into a rough kiss. It’s sloppy, and not at all how Castiel usually likes his first kisses with prospective bedmates to go, but there’s something actually nice about it. If he had the time, and didn’t have the threat of Raphael over his head, Castiel thinks he might actually like to put an effort into bedding Dean Winchester.

That having been said, they’ve only just gotten to the good part, meeting tongue to tongue, when Raphael clears his throat from his place in the alcove’s entrance. The reluctance to pull away is no act on Castiel’s part, and judging from the split second look he gets of Dean’s face when they separate, it’s no act for Dean either. Dean’s apparently figured out Castiel’s plan because he keeps his face hidden, choosing instead to distract Castiel by actually sucking a line of hickeys onto his neck. When Castiel drags his eyes up to meet Raphael’s, it’s to an unimpressed stare. “Keeping ourselves busy, Castiel? Surely this is only a minor interruption.”

Castiel fights the urge to roll his eyes, and Dean takes the opportunity to bite at the underside of Castiel’s jaw. “I’m allowed my breaks, Raphael. Michael doesn’t care what I do with my spare time so long as the end result is what he wants. You should know that better than anyone.” Raphael purses his lips, but Castiel really doesn’t have the time to think on it because Dean’s managed to loosen his tie and undo the top three buttons of his shirt. Currently, the P.I. he’s supposed to kill is biting up his collarbone while his brother’s right hand man watches, completely oblivious as to who’s in the alcove with Castiel. This is the part where Castiel takes back the wish that he’d killed Dean when he’d had the chance.

“So long as it gets done, Castiel,” Raphael says ominously, pulling Castiel away from the wonderfully warm mouth marking him for a few moments. There’s really nothing else for either of them to say, so Raphael leaves, letting both curtains close the alcove behind him as he does.

It’s not completely dark in the alcove, but it’s dark enough that Castiel has trouble seeing Dean. As soon as he’s certain Raphael won’t come back, Castiel rests a hand on the back of Dean’s head. “You can stop now,” he says, though it doesn’t quite sound as steady as he’d like it to.

Dean finishes sucking one last hickey before standing up straight to try to meet Castiel’s eyes in the dark. “So, what was all that about?”

“That,” Castiel says, forcing himself to detach from the situation, “was about me not successfully completing my mission.” The silence that follows tells Castiel that Dean has no idea what Castiel’s talking about. “My assignment to kill you,” he clarifies, as if explaining something very simple to a small child.

Dean nods, a slight shift in the light behind his head the only indication. “The one you didn’t complete because you decided to fix me up and let me continue investigating your older brother.” Castiel nods, even though he’s not sure Dean can see it. “So, all of this - the flirting, the making out to hide my face - what was all that?”

Castiel really wants to shoot himself in the foot when he says, “A game. The flirting was to keep you off balance, the kissing to save my reputation.”

Dean studies Castiel’s face for a long time before finally looking away with a humorless laugh and a sizable step back, dislodging Castiel's hand. “Y’know, you’ve got a helluva poker face there, Cas. I’d hate to be the guy you’re determined to make broke by the end of the night.” It shouldn’t make Castiel’s heart ache to hear that coming out of Dean’s mouth, but it does. Eventually, Dean turns to look at Castiel again. “If we see each other again?”

“Then I’ll have to complete my mission,” Castiel says. “You will die.”

* * *

Sam’s quiet for a very long time after Castiel finishes talking. Castiel isn’t sure what’s going through the younger Winchester’s head, but he knows it isn’t sunshine and rainbows. When he does speak, it’s not at all what Castiel was expecting. “You lied to Dean. Why?”

Castiel blinks. And then he blinks again. “You’re asking me why I lied to your brother, the man I was supposed to kill, about the reasons behind my actions, when the truth would have brought more attention to your brother from mine.” Castiel knocks back his whiskey while Sam stares at him. “That sounds like a ridiculous question.”

It’s obvious Castiel isn’t going to say anything else about the important things he said to Dean, so Sam latches onto the tiny bit of information he got about Castiel’s family. “So, a cousin named Anna? Were you two close?”

“We were as close as family could be when that family is a mob whose very lives are dependent on us not turning on each other,” Castiel answers after a very long pause and another refill of his whiskey. “Dean’s contacts were correct. I am, as last I knew, the youngest Novak, with Anna older than me by barely a year.” When Sam doesn’t look satisfied with this small piece of information, Castiel resigns himself to telling Sam about other members of his family. “Of course, Dean was also aware of my relationships with two of my other cousins, Balthazar and Gabriel, if his contacts were able to find out about Anna.”

Again, Sam perks up like a puppy offered a bone. “You’ve got more family? I mean, of course you have more family, you were part of a mob run by your family. But, you’ve actually got more family that you’re close to? What’re they like?” Sam looks like he wants to ask more questions, but his eyes go wide as he realizes he’s a hair away from rapid firing questions at Castiel before the bar owner can get a chance to answer the first one.

Castiel shakes his head. “Gabriel is the eldest of the four of us, though you wouldn’t guess it by the way he acts. He’s only a few years older than me, and has a protective streak a mile wide, though he’ll deny it if asked.”

“Tell me about it,” Dean says from the doorway, silhouetted by the street lamps along the street behind him. Sam and Castiel turn to look, surprised by the elder Winchester’s appearance. “He’s also got a fondness for grand entrances and candy.”

Sam looks at Castiel, who kind of looks like he wants to punch something, so Sam turns to Dean. “I thought you and Lisa were spending the night together?”

Dean waves a hand, taking a step into the bar. “Nah, Lisa called it a night early. Said the trip took more out of her than she’d thought it would.” He looks to Castiel for permission. “May I?” It takes Sam a while to realize that Dean’s asking permission to come inside the bar.

Castiel unclenches the fist laying on the bartop. “I suppose, so long as you don’t ask me to serve you.” Dean nods, and Sam’s eyebrows shoot up his forehead. He’s never seen Dean act like this around anyone - cautious, tiptoeing on the edge of something. It’s a strange sight, for someone who’s known Dean almost all of his life.

It doesn't seem to surprise Castiel, though he’s the same way. Sam clears his throat in order to clear the, probably sexual, tension in the room. “So, Gabriel. I guess that means that you weren’t the only one to defy Michael to get to know Dean,” he says to Castiel. The bar owner finally looks surprised by something, and Sam has to hide his smile at the sight.

Dean stops in front of the bar, and leans over to grab a glass with a quick wink at Castiel. “I wouldn’t necessarily say _know_ me, Sammy.” Sam rolls his eyes at the childhood nickname, but doesn’t protest against it. “It was more like he ran me down because he was worried about Cas here.”

* * *

**_Eight years earlier_ **

At this point, Dean feels like he needs better security for this office, even if it’s a temp, because he’s really tired of people breaking in. Admittedly, this is only the second person to break in, but that’s still two too many. “Don’t you people have better things to do than hang out in my office?”

The man standing by the window turns around, his face in shadow until he leans over the desk and turns on the lamp. “See, normally I would, but call me cock-eyed, cause I got curious.” He glances at the gun Dean’s aiming at him with an unimpressed look. “You planning on using it or just keeping it out for decoration? Cause, if you’re gonna use it, I gotta tell you - that’s gonna be hell to pay for, all that blood to clean up.”

Dean stares at the lollipop the man’s casually waving around. “You’ve gotta be kidding me.” He sighs and holsters his gun, knowing it's useless. If his guest wants him dead, there isn’t really anything he’d be able to do about it. “What the hell does the Trickster want with me?”

The Trickster grins widely, pointing at Dean with the lollipop. “I knew you were a smart one, Dean-o, even with all this fussing about this random girl and what might’ve happened to her.” He waves the lollipop around in a circle before sticking it into his mouth. “Wouldn’t surprise me if those contacts of your’s managed to find out who I really was.” The Trickster keeps grinning, even as Dean glares at him, apparently without a care in the world.

Even though he’d really like nothing more than to kick the Trickster out and go to bed, Dean knows there’s no way he’s getting out of the Trickster’s game. “Gabriel Milton, member of the Novak mob, cousin to current mob boss Michael Novak,” Dean says like he’s reading off a business card. “Goes by the Trickster when doing non-mob related work, most of which is why Michael doesn’t trust you as much as he should, given your rank in the mob.”

The Trickster, Gabriel, claps his hands together slowly. “Well done, _Mister_ Winchester. Guess there’s a reason Cassie was interested in you after all.” Dean tries very, very hard to ignore the way his heart decides to do a flip in his chest at the drop of Castiel’s name, or nickname rather.

Dean rolls his eyes, like he wanted to do about ten seconds earlier. “What d’you want, Milton? You know I know who you are, you know I know Cas. What’s so important that you had to come all this way to tell me it in person?”

Gabriel’s eyebrows stay planted on his forehead in what looks like a mimicry of a surprised expression. “Cas, you say? I didn’t know anyone outside of the family’d given him a nickname.” Dean doesn’t budge, though he does internally curse himself for his slip of the tongue. “Along those lines, Cassie’s one of the best of us, and I do mean that. He’s a good shot, but he’s also a good person. What he did, pulling you out of the line of fire and putting himself in it? That’s pretty much the definition of his personality.”

None of this is helping to get rid of the pit in Dean’s stomach, so Dean decides it’s best to cut this conversation off now. “Cas already told me his reasons behind everything, so I’d appreciate it if you left and let me get some sleep so I can decide what to do with a clear head tomorrow.”

Something Dean said caught Gabriel’s attention, ‘cause when Dean looked up from the only book in the room, the Trickster was looking at him with an odd look, lollipop back in hand. “And here I was thinking you were smart,” he says, his voice oddly flat in a strange contrast to the playfulness of earlier. “I suppose you think it was sheer luck Cassie was out looking for you the night you got into a firefight with a coupla the mob.”

“What if I do?” Dean’s not sure he likes where this is going, but it’s too late to back down now. Anyway, he’s actually itching to hear the truth, not what Castiel says is the truth five seconds after almost kissing Dean within an inch of his life.

Gabriel snorts out a laugh. “Then you’re as dumb as I thought you were when I first heard about you. What if I told you that I was Cassie’s cover for going looking for you that night?” Dean doesn’t know it, but his mask cracks just the tiniest bit. “I didn’t even know he was on duty that night. We were supposed to go drinking and he never showed up.”

Dean sucks in a deep breath. “What’s that gotta do with me?”

The Trickster shakes his head, a smile on his face that says Dean’s an idiot. “Cassie didn’t just get assigned to kill you, dumbass, he chose the assignment. The assignment which he failed to complete, need I remind you.” Dean’s heart starts racing, and he definitely doesn’t like where this is going, even if his heart does. “How about I just spell it out for you? Cassie chose you over his family.” Gabriel pops the lollipop back into his mouth, moving to leave. “Guess you aren’t as smart as you think you are. See ya around, Winchester.”


	5. we pick this time (to fall in love)

**Notes for the Chapter:**

> yay, just nine days later! also, we get a bit of a breather in the second half because this is the first chapter where i really deviate from the original version of this story.  
> another reason is because i honestly couldn't think of anything else to write that wouldn't make me want to erase it and just leave the chapter at around 1700 words.  
> non beta'd, so all mistakes are mine

“So, choosing me over family.”

The bar’s quiet in the wake of Sam calling it a night, leaving Castiel and Dean alone for the second time in as many days. Castiel’s taken the opportunity to clean up and start to close up shop for the night while Dean stares into the little bit of whiskey left in his glass. Dean thinks that it shouldn’t be this easy to fall back into the camaraderie he had with Castiel all those years ago and before Castiel lied to save Dean’s ass, again. 

Castiel stills when Dean speaks, and he waits for Dean to finish his thought. When nothing follows, Castiel looks over his shoulder and across the bar at Dean. “Did it surprise you, what Gabriel said? He had to have seen you after that night at the club, after you found out who I was.” Castiel’s face is shuttered though his eyes reveal his curiosity.

Dean debates his answer in his head, choosing honesty as the best policy. It’s worked well for him this far, who’s to say it won’t work for him some more. “I can’t say it wasn’t new information, though I should’ve guessed by the way you kissed me.” He shakes his head. “Even now, I can’t figure out what’s going through your head, Cas,” he pauses, “including why you lied to me. Twice.”

The emphasis on ‘twice’ doesn’t go unnoticed by Castiel, the slight twitch of his shoulders enough of an indication to Dean. “I believe you were the final straw, Dean. The assignment that made Michael realize I was never going to be the mindless soldier he wanted me to be,” Castiel says after a long pause. “Gabriel was right in that I chose the assignment to kill you. I think he knew my intentions from the moment he heard that I’d volunteered for the job.” 

Dean leans forward onto the bar, silently willing Castiel to turn around and face him again so that he might get a chance to see what’s going on in the bar owner’s head. “What’d he say?”

* * *

**_Eight years earlier_ **

“Boy, you sure know how to pick ‘em, don’t you, Cassie?”

Castiel rolls his eyes at Gabriel’s dramatics, choosing instead to walk into his kitchen as if his cousin isn’t sitting in his armchair after breaking into his apartment. “Please, Gabriel, feel free to make yourself at home. I’m sure you have a perfectly good explanation for breaking into mine,” Castiel says dryly, flipping on the kitchen light as he prepares to make dinner.

Not two seconds later, Gabriel’s attempting to hover over Castiel’s shoulder, despite being a good four inches shorter than his cousin. “Ooh, what’cha makin’ there, Cassie?” Castiel rolls his eyes again, and Gabriel rocks back onto his heels with a huff. “Touchy, aren’t we? Guess that Winchester must be something to have you all tied up like this.” 

It’s not much, but it’s enough to tell Castiel what Gabriel knows. “I’m surprised Michael would tell you about his request to have the P.I. taken care of, much less who had taken the job.”

Gabriel scoffs. “You seriously think Mike trusts me enough to tell me that sort of shit? No, I’ve got my own ways of finding out information.” He raises his eyebrows in what Castiel thinks is supposed to be a suggestive way. “You would not  _ believe _ the skeletons in the Winchesters’ closet.” Castiel moves across the kitchen, grabbing some spice or another from the pantry but mostly just putting space between the two of them. “You’re not planning on killing Winchester.”

The pantry door closes just a shade too harshly. “What makes you think I have any intention of disobeying Michael’s orders?” Castiel carefully avoids Gabriel’s eyes, knowing that, when Gabriel wants something, he’ll stop at almost nothing to get it. 

“I know you, Castiel.” That more than anything gets Castiel to stop. It’s rare for Gabriel to call Castiel by his full name, and when he does, the Trickster always means business. “And I hope you know what you’re doing, trying to save him like this. You and I both know Michael won’t take this lightly. Winchester’s skirted the edges of the mob’s affairs before, but this is the first time he’s taken a direct interest in the mob. And for him to go after Michael, right off the bat?” Gabriel shakes his head. “You know Michael’s not planning to stop until he’s got Winchester’s head on a silver platter.” 

Castiel turns around, face to face with Gabriel’s serious expression. “Why do you care, Gabriel? You’ve never cared when I’ve disobeyed Michael before. If anything, you’ve almost thrown me to the wolves, rather than help me.” 

Gabriel frowns. “I don’t care about Winchester, I care about you. Michael’s vicious, and if you let Winchester go, you will be hunted down and Michael will make an example out of you. He doesn’t take kindly to people who defy him.” He stares at Castiel, like he’s trying to make his cousin understand what it is he’s saying. “Why’s it so important that you save Winchester? How’s he any different from the dozens of other people Michael’s assigned you to kill?”

For that, Castiel doesn’t have an answer. Gabriel reads it in the line of tension in Castiel’s shoulders, and he frowns deeply. “What I do know is that I cannot allow Dean Winchester to die. Not by my hand, and most certainly not because Michael ordered it,” Castiel says, and Gabriel slouches, his shoulders sloping downwards. 

“When?”

Castiel tries not to look as surprised as he feels by what sounds like Gabriel’s offer to help. “He’s planning on breaking into one of the warehouses tomorrow night, so I was planning to catch him in the inevitable firefight.”

Gabriel nods, still frowning, but apparently willing to help. “If anyone asks, you’re out drinking with me tomorrow night.” Castiel cocks his head to the side, the necessity of the cover story escaping him. “If Michael hears that Winchester escaped a couple of thugs guarding one of the warehouses while you were somewhere else, he won’t think you had anything to do with it.” 

Castiel smiles at Gabriel, a small thing in comparison with some of Gabriel’s. “Thank you, Gabriel.”

Gabriel shakes his head, even though he starts smiling too. “I sure hope Winchester knows what he’s getting into with you, Cassie.”

* * *

Dean stares at Castiel, a small smile playing on his lips. “I guess I did hear right about you, Cas.” Castiel frowns, a furrow forming between his eyebrows at the crypticism of Dean’s statement. “When you went into hiding, apparently trying to save my ass, I found a few people you’d been assigned to kill. Each one of them had a story about how you saved their lives instead, and got them away from Michael before anything else could happen to them.” Dean reaches a hand out to Castiel. “Don’t try to hide from me again, Cas. We both know where that got us last time.”

_ A gun, aimed at the spot between his eyes from behind the door.  _

_ Something Dean swears is crying, but he knows Castiel will never admit.  _

_ “Let me help you, baby.” _

_ “Stay away from me, Dean.” _

Castiel shakes his head. “You were never supposed to find out. You were supposed to hate me for as long as it took.” He rests his hand on Dean’s, not quite taking it but not shying away either. “I don’t understand why you don’t.” 

Dean shrugs one shoulder, adjusting their hands so that their fingers slot together. “Guess there’s a few things even Castiel Novak can’t understand.” Castiel shakes his head again, but this time it’s to hide his amused smile. Dean’s own smile slides off his face as he realizes the time. “I’ve gotta go. Lisa wants to work on more things for the wedding tomorrow, and she’ll kill me if I don’t actually offer up an opinion.” 

“Of course,” Castiel says, sliding his hand out of Dean’s before Dean can stop him. Dean feels the ache in his chest grow as he watches Castiel close himself off again. “You’re going to need as much rest as you can get. I’ve heard wedding planning can be quite the tiring experience.”

Dean wants to say something about how that wasn’t what he meant, about how he’d kill just to stay up the entire night talking to Cas, but he doesn’t. For some stupid reason, he lets Castiel pull away again, even though that was exactly what he’d been trying to stop. Dean sighs, standing to leave. “Night, Cas.”

Castiel’s response is as polite as ever. “Good night, Dean.” 

* * *

Sam barely waits until the sun has risen to make his way back to Castiel’s bar. He feels like there’s things Castiel and Dean aren’t telling him, but he’s not sure how to get the answers he wants out of them. He’s used to this sort of thing from Dean, apparently claiming ‘big brother privilege’ over him, but it’s surprising to get it from Castiel. Castiel can be vague and cryptic, but he’s never outright avoided a topic before.

Or maybe he has, and Sam’s just never noticed it. 

The bar’s front door is open by the time Sam gets there, so he thinks Castiel might’ve been expecting him. Castiel’s presence behind the bar just solidifies the notion for Sam. He’s barely through the door when he starts talking, and even then he’s not sure he knows what he’s saying. “Are you in love with Dean, Castiel?” 

Castiel meets Sam’s eyes with a steady gaze, and Sam’s gotta give him credit for his blank face. “If I say yes?”

Sam shrugs. “I guess I’ve gotta yell at you for not taking the opportunity to not do something about it. I’ve also gotta ask you what the hell you’re thinking in pushing him away like this.”

Castiel nods, like he’s agreeing with what Sam’s saying. “And if I say no?”

“Then I call you out on your bullshit,” Sam says. Castiel blinks, clearly not expecting that response. “I know you, Castiel. Maybe not as well as Dean thinks he does, but we’ve been living in the same town for two years, and I like to think we’ve been friends for at least the past year.” He shrugs again. “If you don’t wanna count that, count on the fact that I know Dean.” 

The bar owner’s shoulders slump. “Then I suppose there’s no hope in trying to convince you that I’m not in love with you brother?” Sam shakes his head. “You wouldn’t be the first one to suspect something anyway. Gabriel, Anna, and Balthazar all suspected something back when Dean and I first met.” 

Sam doesn’t look surprised by this information. “You mean you didn’t announce the fact that the two of you made out in the back of a night club? I’m shocked really.” Castiel gives Sam a dirty look, but it doesn’t change the younger Winchester’s feelings on the subject. “Seriously, Castiel, you made out with Dean to save his ass. Not to mention, you lied to him, more than once, for his own protection. You can’t possibly have ever thought that people wouldn’t have thought you were in love.” 

“Ah, a man after my own heart.” Sam’s not sure how to react when Castiel’s face gets caught up somewhere between relief, annoyance, and fondness. “Cassie, I hope you plan on introducing me to this lovely piece of ass that I am seriously tempted to tap right here and now.”

Castiel rolls his eyes, and Sam finally turns around to see the newcomer. “Sam, allow me to introduce my previously-thought dead cousin, Gabriel.” 

Sam’s jaw may or may not drop open in surprise. “What the hell are  _ you _ doing here?”

Now Gabriel’s the one with a mixed expression, his somewhere between embarrassment and pride. “Hiya, Samsquatch. Long time no see.”

Castiel’s eyebrows shoot up his forehead. “You two know each other?”

Sam glares at Gabriel, who’s trying to shrink into himself while walking into Castiel’s bar. “Yeah, I guess you could say that, Castiel.” Gabriel’s still being glared at while he slides onto a barstool a good five feet away from Sam. “We met about two years ago, right after I graduated from Stanford, just before I moved out here.”

A small smile appears on Castiel’s face when he realizes that Sam’s one of the few people to have cowed Gabriel. He leans on the bartop by Sam, giving Gabriel a sly look as he does. “Feel free to fill me in. I would enjoy to hear of relationship troubles that weren’t my own.” Castiel holds up a finger as soon as Gabriel opens his mouth. “Not a word, Gabriel. Consider this payback.”

Reluctantly, Gabriel shuts his mouth and Sam begins to talk. “I was out celebrating earning my degree, and the bar my friends picked was just crowded enough for not everyone there to be a freshly graduated law student.

* * *

**_Two years earlier_ **

“Cheers!” 

Sam raises his glass of whiskey in a toast along with the rest of his friends, taking a long sip before putting it down. Jess knocks herself against his side, her blonde curls bouncing on her shoulders in a nice contrast to her bright red lipstick. She manages to bring his head down low enough to plant a solid kiss on his cheek. “Congrats, Sam! You made it through!” That sends off another round of cheers through their friend group. Sam raises his glass half-heartedly, smiling at Jess. “So what’s got you so upset?”

“It’s nothing,” he says, but Jess rolls her eyes at him. Sam knows from experience that, when Jess wants to know what’s wrong, Jess is gonna find out what’s wrong. “It’s just that my brother isn’t here.” 

Jess goes up on her tiptoes, despite being one of the tallest people there, and does a sweep of the bar. “Nope, no brooding, P.I. older brother here.” Sam laughs despite himself, and Jess grins. “Why’s it matter if Dean’s here or not? I know the two of you are close, but you can do without him seeing you get sauced for one night?”

Sam laughs again, smiling down at Jess. “Y’know, you’re right. Dean’ll just have to take me drinking on his own time when I see him again.” 

“That’s the spirit!” Jess set off another round of cheers. Just before she was pulled away by their friends, she managed to pull Sam down again and press another kiss to his cheek, leaving two matching red lipstick marks. “Now people’ll know you’re rationed!”

Sam rolls his eyes as he waves her away, setting off for the bathroom as soon as she was engrossed in another conversation. “Rationed, my ass,” he grumbles good-naturedly as soon as he walks into the bathroom, heading straight for the sinks to wash the lipstick off his face. He likes Jess, a lot, but he doesn’t think she’d be willing to move out of town with him.

“Trouble with the dames, huh?” Sam jerks his head up to stare at the stranger in the mirror in front of his face. “Unless it’s trouble with the fellas?” His hand jerks towards his side, where he usually keeps his gun holstered. Unfortunately, it’s not there since he wasn’t planning on getting involved in a firefight tonight. The stranger holds up his hands. “Woah, big guy, take it easy. I didn’t mean anything by it.”

Sam stares at the stranger incredulously. The silence stretches out long enough that the stranger apparently gets some sort of sugar craving, pulling a piece of candy out of his pocket, unwrapping it, and tossing it into his mouth all before Sam thinks of something to say. “What makes you think I’m having some troubles?”

The stranger raises an eyebrow. “So, I didn’t just hear you say ‘Rationed, my ass,’ because, if you’re willing, I’d be happy to take you home for the night.” 

Sam continues staring at the stranger. “You don’t even know my name.”

“Fair point,” the stranger replies. He holds out one of his hands, sending Sam a winning smile. “Call me Gabe.”

“Gabe,” Sam says slowly, eying the stranger’s hand. When that’s all Sam does, Gabe wiggles it a little. It makes Sam laugh, and he gives in, shaking Gabe’s hand. “I’m Sam.” 

Gabe keeps smiling at Sam, even as he takes his hand back. “Well, Sam, how about it? You wanna blow this popsicle stand with me?” 

Now it’s Sam’s turn to raise an eyebrow, feeling just dangerous enough to be willing to spend the night with this man. “Don’t I get a kiss before we get any further?”

He laughs when Gabe eyes their height difference. “You’re gonna have to come down here if that’s what you’re looking for, Sammy.” Sam feels his smile slip away at the unintentional reminder of why he was upset earlier, and Gabe seems to notice it. “Not a Sammy, huh? Guess I’ll just have to come up with some other names to call you.” 

Sam rolls his eyes. “Get up here. I wanna know what candy you’re eating.”

* * *

Castiel looks two seconds away from covering his ears like a kid who’s heard his parents having sex. “I take it you went home with Gabriel then.”

Sam side-eyes Gabriel, the Trickster’s smug smile falling away at the look. “More like I took him home with me, since I didn’t feel like spending the night in a hotel room. He stayed the night, made me breakfast in the morning, then took off with only a ‘I had a good time, sweetheart’ in his wake.”

Castiel let out a low whistle, turning to his cousin. “Is this true, Gabriel?” To Castiel’s clear surprise, Gabriel grins almost sheepishly, answering the question without having to say anything. “I can’t say I’ve ever heard of you being anything less than courteous to your lovers, one night stands or not.”

Gabriel clears his throat. “Well, when you realize you’ve just bedded Sam Winchester, you start to get a little antsy, especially when you know his brother’s on Michael Novak’s hit list.” He looks back at Sam, still looking a little nervous. “If you’d like to hit me, this is the perfect opportunity.”

Sam shrugs. “It depends. If you hadn’t known who I was or if Dean wasn’t wanted by the Novaks, would you have had lunch with me that day?” Castiel’s head swivels back towards Gabriel, excited to see his cousin’s reaction. 

“If I say yes, are you going to hit me?” Castiel considers Gabriel lucky that Sam doesn’t tackle him to the floor as the younger Winchester all but throws himself at the Trickster, hugging him tightly before settling onto the barstool beside Gabriel. 

Castiel has never seen Gabriel look at anyone like that before. “And here I was, thinking I would have to introduce the two of you to each other.”

“You know, you’re doing very well for someone who just realized one of his closest relatives wasn’t dead after eight years,” Gabriel comments to Castiel, finally tearing his eyes away from Sam.

Castiel shrugs. “The man I fell in love with eight years ago showed up on my doorstep two days ago, after I specifically told him to stay away from me. Finding out you’re alive isn’t the most surprising thing that’s happened to me.” 

Sam nearly falls off of the barstool, laughing at the offended look on Gabriel’s face. 

**Notes for the Chapter:**

> so, gabriel! i always liked him, even though he's introduced as an asshole in the series.  
> i have legitimately no idea when chapter 6 might be finished and posted because i move back to school in a week and i'm working a show that goes up at the end of september, but hopefully sometime in the next month i'll be able to find time to write the next chapter.  
> kudos and reviews are welcome!


	6. i cannot (ever see you again)

**Notes for the Chapter:**

> sorry! i know it's been three weeks but i've been back at school and i'm working a show and motivation has been lacking, so this chapter's been slow to come together. it's also one of the shorter ones, so i apologize about that. i don't know when i'll have chapter seven up, so i'll apologize about that in advance.  
> anyway, i hope you enjoy

“Something’s bothering you,” Lisa says, sitting across from Dean in the diner booth where they’ve settled for lunch. She might’ve known Dean for seven years, but even she has trouble reading his moods sometimes. _Sam’s probably never had this problem_ , Lisa thinks to herself. _Hell, someone across the street could probably read his face better right now_.

Dean can’t say he’s too upset about Lisa’s inability to read his mood right now, cause he might actually take a bullet to the head if she ever figures it out.

_“I wanted to see you.”_

_The shriek of curtains being pulled shut on a metal rod. “You’re an idiot for coming. Do you have any idea how much danger you’re in?” He crosses to the figure by the door. “How did you even find me?”_

_“Actually, the funniest thing happened. I went home last week and this cranky Brit showed up on my doorstep, complaining about his cousin who was unbearable mopey because of having to hide from his family and some smartass P.I. who was too stubborn for his own good.”_

Dean shakes his head, trying to muster up a smile. “It’s nothing. Just my past coming back to bite me in the ass.”

Lisa’s got that look on her face, the one where she purses her lips and narrows her eyes like if she tries hard enough she thinks she’ll be able to see whatever it is that’s going on in Dean’s head. “This has something to do with that dark haired, blue eyed bombshell you try not to talk about, doesn’t it?” Based on the way Dean’s eyes go wide, Lisa thinks she guessed right. “Which means you’re probably having second thoughts about the wedding,” she continues, and this time Dean almost jumps out of his seat.

“What? No, of course I’m not having second thoughts!” He frowns at her, suddenly worried. “Are you having second thoughts about the wedding?”

Lisa shrugs half-heartedly, but she knows she can’t put this off any longer. “It’s not that I don’t want to marry you,” she starts when Dean slumps back into the seat. “It’s just - alright, how about this. Do _you_ want to marry me?”

“Yes.”

“As much as you did when you asked me?” Lisa knows she’s got him when he opens his mouth to reply before he actually stops to think about it, her hand still up in the air to keep him from making a rash decision. “I do love you, Dean, but I don’t think I want to marry you. Besides, here’s another thing. When was the last time we actually kissed, let alone had sex?”

Dean thinks about it, and he feels his eyebrows shoot up when he realizes how long it’s been. “A month? Has it really been that long since we last kissed?” Lisa shrugs again, like this doesn’t surprise her at all. Meanwhile, Dean seems to be rethinking his entire life up until this point. “I just think it might be a good idea if we hold off on the whole wedding thing if neither of us are that certain that we want to get married, let alone to each other.” She reaches across the table to hold on of his hands. “Okay?”

It feels like an eternity passes before Dean gives her some sort of reply. “Okay,” he says, tension bleeding out of his shoulders as he does.

Lisa smiles at him, and she feels the weight off of her shoulders too. “So, now that we’re not going to get married, tell me more about this person that you’ve been in love with the entire time we’ve been together.”

Dean jerks his knee and rams it into the underside of the table, much to Lisa’s amusement. “I thought we were never gonna talk about that.”

“Well, let’s be honest here. We’re not so much as dating as renting an apartment together, are we, which means that we’re not girlfriend and boyfriend, just two friends who happen to live together.” Her smile turns wicked as she continues. “Which means I earn roommate teasing rights, _finally_. So, talk to me.”

Dean’s saved from having to actually say anything by the appearance of their waitress. They rattle off their orders, and as soon as the waitress walks away, Lisa turns back to Dean expectantly. He sighs, and Lisa knows he’s giving in. “I met him a few months before I met you,” he starts, only for Lisa to immediately gasp in surprise. “What?”

“I didn’t know it was a man,” she says, not disgusted or alarmed, just surprised. “I guess I always pictured a pinup girl covered in pie.”

Dean rolls his eyes when Lisa grins, but he keeps going anyway. “He’s stubborn with an unusual brand of humor, and he’s…” He stops when he realizes what Lisa’s actually asking. “Yes, Lisa, he’s a dreamboat. You happy now?”

Lisa shrugs. “I’m just glad he’s attractive enough for you to still call him a dreamboat after not seeing him in so long.” Dean hesitates just long enough for Lisa to realize what’s bothering Dean. “You’ve seen him recently, your dreamboat. He’s in town?”

Dean nods. “Yeah. He’s a friend of Sam’s. I didn’t know until I ran into some trouble my first day here. I -” He stops, the wheels turning in his head. “Holy shit,” Dean breathes, and Lisa furrows her eyebrows.

“Dean? What’s wrong?” She knows the look on his face, because it’s the one she sees whenever he’s just cracked a case. It’s certainly not a face she’d be expecting while they’re talking about the love of Dean’s life, who she’d known hadn’t been her from the moment they got serious.

Dean shakes his head, sliding out of the booth. “Sorry, I just figured something out. I gotta go take care of something.” He pulls out his wallet and tosses her enough money to cover their lunch bill. “I’ll catch up with you later, alright?”

Before Lisa can even nod, Dean’s out of the diner.

* * *

Castiel’s seen Dean’s bright fury before, but he doesn’t think he’s ever seen the P.I. like this. Dean barely checks to see if the bar’s empty before slamming the front door shut behind him, flipping the sign from OPEN to CLOSED with enough force that Castiel is surprised the glass doesn’t crack. “You knew who Sam was as soon as you met him, didn’t you?”

There’s no right way to answer that. He knows that Dean knows that the Novaks are thorough - Dean would’ve discovered that in the original case that brought him to their attention. Castiel doesn’t know why Dean even bothers to ask the question, but he can see that Dean has something he needs to get off of his chest, so he pushes. “No, not at first.”

“C’mon, Cas, you can’t give me any bullshit about not knowing about my brother.” Dean turns to face him, his expression hard set and a steely look in his eyes. “The Novaks don’t slack on their research, and that’d be one of the first things you found out about me.”

“I didn’t say I didn’t know about him, I just said I didn’t know who he was as soon as I met him.” Castiel meets green eyes, the calm to Dean’s storm. “It was actually several weeks before I learned his name. But yes, I did know you had a brother.”

Instead of looking calmer, Dean looks angrier. “And you didn’t _say_ anything? I would’ve been one letter away, and you didn’t bother mentioning to Sam that you saved my life?”

“It wasn’t as if our families were a topic often discussed.” Castiel forces himself to keep from crossing his arms over his chest. A defensive position is the last thing that would help him right now. “Sam mentioned he had a brother a few times, but most of our personal discussions were about work. He would talk about his coworkers and I would trade stories about customers.” There’s a wry twist to his lips. “There was never a time to say ‘By the way, I saved your brother’s life after almost killing him and then almost got him killed.’”

Dean doesn’t say anything to that, but Castiel’s starting to think there’s something else the matter here. After all, there’s really only one question Castiel’s never answered, and that’s the one Dean wants an answer to the most.

“You want to know why I didn’t let you come with me.”

Castiel’s glad no one else is there, because their staring could be awkward for anyone else. “No,” Dean finally says, but Castiel doesn’t let his surprise show. “I wanna know why you didn’t even bother telling me you were leaving. Why someone else had to tell me.”

It takes a surprising amount of effort for Castiel not to step back, pieces falling into place like a puzzle. “Anna,” he says, and Dean nods.

* * *

**_Eight years earlier_ **

“He’s gone.”

Dean spins around, aiming his gun at the woman who spoke. She smiles, almost motherly at him, the sunlight turning her red hair an almost golden color. It takes a minute for him to recognize her, the presence of color throwing him off more than anything else. “You’re Anna,” he says after a moment, not sure if he should holster his gun or not.

She nods, and holds her hands up to show that she’s unarmed. Dean doesn’t take it as a surrender, but he does put his gun away. “You’ve come looking for Castiel, but I can’t tell you where he is.” Dean opens his mouth to ask her why not, and possibly threaten her, but Anna smiles again. “He’d have my head if he knew I was the one who told you,” Anna says gently. “He’d have my head if he knew I was talking to you at all.”

Dean stares Anna down, but her face is just as hard to read as Castiel’s is. “Then why are you talking to me? Why’re you telling me any of this?”

“Because you care about him,” Anna replies. “And he cares about you. I know you’re angry with him,” she continues when Dean still looks ready to fight her, “but he’s doing this because he worries about your safety. Do you have any idea how much trouble he’s in right now?” Dean feels some of the blood drain out of his face as he mentally reviews what he knows about the woman he was trying to find.

Michael Novak had had almost every person in his mob looking for her, and she was just a minor annoyance.

“Cas turned his back on Michael, and Michael’s willing to burn the world down just to find him,” Dean says faintly, the realization settling like a weight in his stomach. Anna nods, which does absolutely nothing to comfort Dean. “You tryna tell me I’ll never see Cas again?”

Anna purses her lips, considering her options. “I can’t say that for certain, Dean, but I also can’t guarantee that you will see him again. Michael’s vicious when it comes to this type of thing, and Castiel knows that better than anyone. He’s been at Michael’s side for a very long time, but this also means he knows how to avoid his brother.” She tilts her head slightly, and her hair shifts to a different shade of orange-gold. “Curious, that you care for Castiel despite his harsh words towards you. You’re an unusual man, Dean.”

Dean shrugs, trying not to take any pride in Anna’s words. “What can I say, I’m a one-of-a-kind.” Anna smiles at him again. Just as Anna turns to leave, Dean goes, “Wait.” She waits for Dean to gather his thoughts, whatever message he wants her to give Castiel. “When you see him, tell him I’ll keep looking. Michael might be a pain in the ass, but he can’t rule the entire world. Sooner or later he’s gonna give up, and I’ll be there when he does.”

* * *

Castiel knows he doesn’t look nearly as surprised as he should when Dean finishes telling him this, but it wasn’t as if Anna hadn’t eventually come clean to him. She’d told him that Dean was looking for him and she’d told him that Dean wasn’t going to stop. That was when Castiel knew he had to keep Dean at more than an arm’s length away - more like put three city blocks between them.

Now he knows that Anna’s the one who told Dean he was gone in the first place.

Dean’s still staring at him, waiting for Castiel to say something, anything really, that would justify him being quietly angry about this for eight years. “I didn’t tell you because the last time we talked before I left, and before you found me, you decided violent action was the best way to get the answers you wanted.”

That’s enough to crack Dean’s mask a little, the P.I. wincing as he remembers throwing Castiel against a brick wall - a lucky shot, really. If Castiel’d been prepared, Dean would’ve been knocked flat on his ass before he even knew Castiel was in the same place.

They both know that Dean was lucky to get out of that fight with only a few scrapes and bruises.

“Do you understand why I did it?” Dean’s voice is quiet as he asks the question, quieter than Castiel’s ever heard it. “Why I went after you, Cas, even after everything you said to me? After everything you did to me? Hell, you probably could’ve broken my arm and I still would’ve looked.”

Castiel leans against the bar, fairly certain that Dean isn’t in the mood to punch him anymore. “Yes, Dean, of course I understand. But that’s also exactly why I couldn’t let you follow me. It’s why I couldn’t let you any closer than I already had.”

Dean sighs and makes his way over to the bar, sitting on a stool. “You sending that record really didn’t help.”

“I thought you might like the music.” Castiel shrugs. “Obviously you did, if the first thing you do is try to serenade me with one of the songs after getting knocked out by your brother.”

A hum is Dean’s only response for a long time. Just when Castiel’s thinking about opening the front door and flipping the sign over, Dean stands and offers Castiel a hand. When all Castiel does is stare, Dean shrugs. “Dance with me, Cas?”

Not for the first time, Castiel wishes he knew what was going on inside Dean Winchester’s mind. And, not for the first time, Castiel ignores his head and lets his heart lead the way.

He puts his hand in Dean’s and walks around the bar to fulfill an eight year old dream.


	7. aren't you the kind that tells?

**Notes for the Chapter:**

> okay so sorry for the three week wait, and the fact that this chapter is sorta short and suckish because i've been writing humor for the past month and my brain did not want to do angst which was what was supposed to happen here but didn't really so that's why it's short and bad  
> also! there is an end in sight, the end of the tunnel is nigh and i am so sorry that it is taking this long to write this out. i am suffering writer's block big time because my creative writing class is sucking out all of my creative energy. plus i just worked a show for a month, but it's closed now so i can breath and hopefully put out a better chapters 8 and 9 before Thanksgiving  
> yay!

The quiet’s broken by gunshots down the street, and Castiel lays his head against Dean’s shoulder. “I thought you were the only person in town being hunted by the mob,” he says in a tired voice. Dean laughs, and more gunshots ring out anyway.

“Nah. Last I knew, the mob was after you too,” the P.I. responds, and Castiel rolls his eyes.

Of course, neither of them are expecting the familiar face that races towards the bar, blood obviously running down one of her legs.

“Dean!” Lisa calls once she reaches the front door, leaning heavily on the doorframe.

“Lisa?” Dean pulls away from Castiel, not without some hesitance, to help Lisa into the bar. She leans on him heavily as she actually takes in their surroundings.

“Castiel?” Lisa’s questioning tone makes sense when Dean looks away from where he’s trying to get Lisa into a chair to where his ex-fiancée and the bar owner are staring at each other like they’ve just seen a ghost.

“Lisa?” Castiel asks, and Dean’s a little slow in the uptake as he realizes that he might not know everything he thought he knew about Lisa if Castiel recognizes her.

Heavy footsteps follow Castiel’s question, and Dean doesn’t have to turn around to know who they belong to. Lisa asks, "Sam?” like she needs another set of eyes to confirm what she’s looking at.

“Castiel?” Sam looks at the bartender expectantly, and Dean doesn’t notice the pair of feet standing slightly behind his brother as he looks at Castiel too.

“Dean?” Castiel asks as he looks back at Dean, this having turned into a complete shitfest.

“Cas?” Dean asks right back, even though both of them look just as confused as the other.

The fifth person finally makes themselves known with a dramatic flair, unsurprisingly. “Dean-o!” Gabriel steps out from behind Sam to grin at the P.I., and Dean wonders when the hell his life got like this.

Lisa looks between the four men in the room, one hand pressed to the bullet wound in her leg and the other gesturing between them. “I guess we don’t need to do introductions?”

Dean sends Lisa a flat look. “No, but I think you might have to do some explaining.” Lisa grimaces in embarrassment and then in pain as Dean renews the pressure on her leg.

Castiel steps around the bar to grab something to clean Lisa’s wound. “Can that wait until after we’ve dealt with the men trying to kill me?” Lisa asks, sounding far more tired than she had a few minutes earlier, though that probably has something to do with the blood loss.

“Sam, Gabriel, close the door behind you,” Castiel orders, and they do as their told. He comes out from behind the bar top to kneel in front of Lisa, a bottle of whiskey in his hand. “You may want to find something to bite on,” he advises her.

Lisa shrugs one shoulder, trying to smile. “I think I don’t deserve one, after keeping everything from Dean here.” Castiel looks like he wants to advise her against it, but she nods for him to go ahead and do it.

Sam closes the door just as Lisa starts half-yelling half-groaning in pain. “Maybe we should go,” he says, grabbing Gabriel by the arm as he does. Dean looks away from the top of Castiel’s head to send his brother a glare. “Or we could stay and help out with whoever’s decided that shooting Dean’s fiancée. That works too.”

Castiel looks away from where he’s wiping excess whiskey away from the bullet wound up at Dean. “Lisa is your fiancée?” Dean’s expression is almost sheepish when he nods in confirmation. “Only you could attract someone who has just as much as a death wish as you do, Dean.”

“While this all sounds incredibly interesting,” Gabriel interrupts from his position at the front door, looking out the window. “Does anyone mind telling me why Mikey is on his way over here?”

Sam almost pushes Gabriel out of the way to see who it is the shorter man’s talking about. “What? Mikey?”

“Oh God,” Dean says. “Michael Novak is here.”

* * *

“How in the hell did you end up luring Michael Novak to a place where four of the five people present are on his shit list?”

Lisa glares up at Dean as Castiel works on tying fabric around her leg. “It wasn’t like I did it on purpose, Dean. I don’t even know how he found out we were here.”

Castiel grimaces at that, standing from where he’d been kneeling. “That may be my fault, Dean. I _have_ been here for several years and I didn’t use an assumed name when buying the bar. It’s entirely possible that he found me and, in the process, found the rest of you,” he says, putting the whiskey back on the bar top.

Dean rolls his eyes. “Fan-freaking-tastic. We’ve got the head of the Novak mob out there and we’re basically sitting ducks. Any suggestions?”

“Mister Winchester,” a voice from the street outside calls. Everyone inside the bar freezes before they get the chance to continue their conversation. “A word, if you would be so kind.”

Dean steps away from where he’s been standing beside Lisa, avoiding looking any of them in the eye. “If you’re going to do something stupid, you may as well tell us now,” Castiel says, hurt evident in his voice. He rolls his eyes when Dean just tugs on his vest, straightening it, and adjusting his hat on his head.

“I plan on coming back,” Dean says, after Sam and Gabriel have stepped out of his way and away from the front door. He grins at them, and then just at Castiel. “I’ll let you have the killshot though, Cas.”

Then Dean walks out the door, shutting it with a _thump_ behind him.

Gabriel steps up to Castiel’s side, the two of them staring at the front door. “Are you gonna do it?”

Castiel doesn’t answer his cousin and walks up to the door, leaning against the frame heavily once he’s close enough. It’s enough of an answer for Gabriel, even if it isn’t for Sam or Lisa.

* * *

If Castiel styled his hair a little differently and wore all black, it would be painfully obvious that he and Michael Novak were brothers. As it is, it’s the little things that makes Dean realize for certain that this is Michael Novak standing in front of him. Their eyes are similar shades of blue, both of them have dark hair and fair skin.

But Castiel’s slightly taller than Michael, and broader in the shoulders. It doesn’t make Michael any less imposing.

“Mister Winchester,” Michael says in a friendly tone, although his face makes it clear how not friendly his thoughts are, at least to Dean. The four men holding up Tommy guns might also have something to do with that impression. “It’s a pleasure to finally meet you.”

Dean offers Michael a quick smile, the one he gives men he’s about to punch in the face. “Can’t say the same about you, Mister Novak. You’ve given me a lot of trouble for these past few years.”

Michael’s eyebrows shoot up his forehead. “Me give _you_ trouble, Mister Winchester? Oh no, I’m afraid it’s the other way around. After all, you’re the one who somehow convinced my brother Castiel to let you live.”

For a moment, Dean thinks Michael’s joking. Then, he realizes that the mob boss is completely serious. “It’s been eight years, and you think I’m the one who made Castiel go on the run? How fucking stupid are you?” Michael blinks and Dean continues talking. “I didn’t say anything to convince Cas to help me, he’d already made up his mind by the time we met. He was the one who ran from you, on his own, because he knew there’d be hell to pay if he went back to you.”

Michael’s eyes narrow dangerously, but Dean’s never been one to pay attention to that sort of thing.

“How could you think that that was a good idea? Making your brother, your brother of all people, kill people left and right just because you didn’t like them?” Dean refrains from throwing his hands into the air. “I just can’t wrap my head around it.”

The mob boss rolls his eyes. “I suppose you think we should all treat our brothers like how you treat your’s, with an unhealthy amount of dependence and the ability to shoot a gun at an age where most children can barely feed themselves,” Michael replies, sending Dean a dry look.

Dean doesn’t hesitate before he pulls his gun and aims it at Michael. “You lay a finger on my brother and I won’t give your’s the chance to kill you,” Dean says, his voice steady and calm.

Michael holds his hands up, palms facing Dean. “You don’t need to worry about me, Dean. I’ve got people who do that sort of thing for me,” he adds with a smirk. Michael gestures with two fingers for Dean to put the gun down and he does, glaring at Michael the entire time. “Besides, I didn’t come for you, Dean. I came for my little brother.”

“I really don’t think he wants to see you,” Dean says, and Michael picks up on the almost glad tone in it.

“Why?” Michael glances at Dean as he passes him. “Think he’ll come running back like the good little soldier he is?”

The door to the bar opens, and Castiel looks at his brother for the first time in eight years. “No,” he says to Michael’s surprised face. “He’s worried I’ll kill you without you knowing who pulled the trigger.”

Michael has just enough time to grin before Castiel puts a bullet between his eyes, and then the Novak head falls to the ground.

“Well, that was dramatic,” Gabriel says from his place behind Castiel.

“Shut up, Gabe,” Sam and Dean say at the same time.

Castiel steps out onto the street, over Michael’s body, and looks at the four men Michael had brought with them. All of them look at each other, waiting for someone else to make the first move. “I suggest you four run along now,” Castiel says, his voice deeper than normal.

It’s enough to send the men scampering off down the street.

Once they’re all done staring off into the middle distance, they turn back around to find Lisa staring at them all very disapprovingly. “Hello? Shot in the leg, in immense amounts of pain? Can someone please call an ambulance?”


	8. here's looking at you, baby

**Notes for the Chapter:**

> guys!!!! i am so sorry!!!!!! but the new chapter is done, one month later! i was really hoping to have this finished like two weeks ago and then i got killer writer's block (which is supes awkward when you're a creative writing major) and then i started nanowrimo and got writer's block for that and was like "oh hey maybe i should finish that chapter" and then i did!!!!  
> (please don't kill me. do enjoy this sappy shit though)

For one, very long moment, Castiel thinks that Dean will stay at the hospital with Lisa, fall back into her arms like he thinks the P.I. must’ve done so many years ago.

He can’t lie to himself and say it doesn’t hurt. Not this time, anyway.

Sam’s giving him a look that is far too knowing for Castiel’s tastes, so he makes to leave the waiting room before he can get his heart broken all over again. Gabriel’s just as bad when Castiel passes him, though luckily he doesn’t try to push or make any sort of joke like he would normally.

Dean stops him just as he’s about to reach the doors. “Where do you think you’re going?” He glances between Castiel and the door, and Castiel knows that Dean’s figured out his train of thought by now.

“Back to my bar. I have to make sure the police haven’t ruined too much of  it,” Castiel lies, the words bitter on his tongue.

For a moment Castiel thinks Dean’s gonna ask him to stay. Then Dean nods, albeit slowly, but he still nods. “Alright. I’ll be back there as soon as possible, okay? We’ve still got things to talk about.”

Castiel nods, though he isn’t sure he agrees, and continues out the door. It’s gonna be a long time before he gets much of anything done today, if at all.

* * *

**_Nine years earlier_ **

Castiel must admit, he admires whoever just tried to take Michael’s head off with a sniper rifle. That takes guts and willingness to put one’s own life in more danger than they were probably expecting, given the haste with which Michael dispatched essentially all of his men, Castiel included.

While most of Castiel’s “colleagues” set about checking the nearby buildings - clearly they thought they were dealing with someone who didn’t know what they were doing - Castiel goes a little further, and doesn’t start checking buildings until he gets five or six blocks away. In the third building he checks six blocks away, he finds what he’s looking for, kneeling on the ground and apparently packing up their sniper rifle.

“I don’t think I have had the pleasure of seeing you since you favoured me with those attentions as I lay on the ledge above the Reichenbach Fall,” Castiel quotes, aiming his pistol at the back of the culprit’s head. It’s a shame to use the reference on someone who probably won’t get it, but Castiel says it anyway. He keeps the gun aimed even as the would-be assassin turns their head toward him slightly.

“You cunning, cunning fiend!” the woman quotes back, and it startles Castiel enough that he starts to lower the gun from her head. It gives the woman an opening to twist around, hit at Castiel’s arm, and chop into his elbow to make him drop the gun.

When he recalls the following fistfight, Castiel remembers very little of the exact movements each of them made. What he does remember is both of them pulling knives on each other at some point and coming to a draw when they had knives at each other’s throats.

Castiel glances down to where the woman’s arm is tense and fully extended toward his neck, then to where his arm is an almost exact mirror image. “Promise not to start fighting me again if I take this away?” he asks, eying her face skeptically.

The woman tilts her head slightly, away from the knife, but otherwise her face doesn’t change. “Only if you promise to do the same if I take mine away,” she replies, and Castiel gives a tiny nod of agreement.

Almost simultaneously, they bring their knives away, though they don’t actually put them away. “So what now? I doubt you’re going to let me go,” the woman says, her fingers tight around the knife’s grip.

Castiel contemplates the woman for a long moment, taking in her sensible work shoes to her dirty skirt all the way up to the tight curls, pinned close to her head. Then he puts his knife away, sliding it back into its sheath in one of his coat’s inside pockets. “That sounds like a plan, if you’re willing to keep running for the rest of you life,” Castiel says once he’s looking at the woman again.

She gapes at him, unwilling to look away from his face. “You can’t be serious.” Castiel tilts his head to the side, as if to say ‘why not?’ “Are you insane? Michael Novak is one of the most dangerous men in the country, and you’re willing to just _let me go_? Why? And don’t say a change of heart or some shit like that,” the woman says just as Castiel opens his mouth to answer her.

He raises an eyebrow, silently asking her if she was finished and speaking when she didn’t say anything else. “You beat me, fair and square. You’re better off somewhere else in the world instead of lying in a ditch or at the bottom of a lake. Unless you want me to kill you?” Castiel reaches for his gun, laying innocently on the group a little under two feet away.

The woman’s answer is clear in the way she takes a step forward, her knife raised in offense again. “You’re insane, you know that?” she says, returning to packing up her rifle once she’s sure Castiel won’t shoot her in the back.

Castiel smiles a little at that. “You wouldn’t be the first to say so,” he replies, thinking of Gabriel. Neither of them say anything until she’s done packing and about ready to walk out of the building and as far from Novak territory as possible. “My name is Castiel,” Castiel says, though he isn’t sure why.

The woman eyes him suspiciously, obviously considering whether or not to deign Castiel some sort of response. “Lisa,” she says after a long pause. Castiel nods again, and Lisa turns on her heel, walking out of the room.

Castiel follows almost five minutes later. As Michael insists the hunt for his would-be killer continue, Castiel keeps an ear out for any reports of a Lisa that pass through. There’s one, a Lisa Braeden, who a lot of the other guys seem to think is responsible, so Castiel manages to get their attention redirected to another person entirely. It’s not long before the memory of Lisa’s attempt is replaced by the threat of a straight laced P.I. rolling into town, and heading straight for the Novak’s doorstep.

* * *

Castiel isn’t sure how Dean gets him to tell the story of how he and Lisa knew each other, however brief their acquaintance was. When Castiel finishes, he looks up to find Dean looking at him with a thoughtful look on his face. Castiel waits for Dean to say whatever he needs to, trying not to focus on all of the ways in which Dean could have a negative reaction to this revelation.

“I gotta say, I definitely did not see that coming,” Dean says finally, running a finger around the rim of the glass in front of him. “Thought I was special, Cas, all those years ago when you pulled me out of the firefight. Turns out I was just another in the latest string of rescues.”

“Dean,” Castiel says, reaching across the bartop to grab Dean’s hand, resting beside the glass. “You have to know by now that you’re different.”

“Oh yeah? How?” The look in Dean’s eye is challenging when he meets Castiel’s eyes again.

Castiel gestures around them with his free hand. “Look around you. I wouldn’t be here if I’d never met you. I’d probably still be under Michael’s thumb, following orders like a soldier and only disobeying in the smallest of rebellions.”

Dean downs the rest of his drink before continuing. “Alright. Then why’d you leave the rest of us at the hospital while you came back here to sulk?”

“It wasn’t my place to stay,” Castiel manages to say without his voice giving away any of his hurt.

Dean stares at Castiel, not understanding why the bar owner is so upset. “What do you have against Lisa? Is it because she tried to kill Michael almost a decade ago?”

Castiel scoffs, like he’d hold that against anyone. He doesn’t know where this fresh wave of anger comes from, but he uses it to fuel his next statement. “No, it’s because I am the person who saved the woman who brought you into my life in the first place!” His shoulders slump, and he lets the truth come pouring out. “Lisa Braeden, daughter of Ben Braeden, the man who sent you looking for his daughter, last seen in Novak territory.”

Dean’s quiet for a long moment, and he turns to the bar’s front windows. “It’s raining,” he says, a hair too casually to be a smooth non-sequitur.  

Castiel stares at Dean, tired of running circles around Dean’s thoughts. “So?”

The P.I. shrugs one shoulder, still too casual. “It was raining when we met.” Dean doesn’t turn around to see the confused look on Castiel’s face. “Lisa’s called off the wedding, said it had something to do with us not being completely honest with each other.”

Castiel slumps his shoulders, curling in on himself slightly. “I see. I assume this has something to do with me?”

“What?” This time Dean turns to look at Castiel, now mirroring the bar owner’s confused expression. “Oh, no, I told Lisa I was in love with someone else when we got serious, and she never expected that to change. She said that if I fell in love with her that it’d be fine, but it’d be just as fine if I stayed in love with the other person.”

Leaning a hip against the bar, Castiel crosses his arms, a furrow between his eyebrows. “I’m very confused.”

Dean obviously refrains from rolling his eyes. “She called it off because she felt bad about never telling me about her past involving with the Novaks. Can’t really say that I blame her, given how honest I was with her.”

Castiel blinks. “Oh.” He narrows his eyes after a second. “When you came here, yelling at me about Sam, you seemed determined, as if you’re engagement had already come to an end.” Dean rubs at the back of his neck, and Castiel knows that he has Dean caught. “It _did_ have something to do with me, didn’t it?”

“Yes,” Dean says with a soft sigh. “But it’s not what you think. I was fine with everything the way it was, and then Lisa brought up the fact that we haven’t kissed in over a month. She wanted to call it off because she didn’t wanna marry me anymore, not because I was in love with someone else.”

There’s another long pause, then Castiel says “Oh” again. “Well, that’s different.” Castiel pulls his hands back to himself, interlacing his fingers together while he watches. “So, does this mean - is Lisa no longer an obstacle?”

Dean’s the one to reach across the bar top this time, taking one of Castiel’s hands in his own. “No, she’s not.” He smiles at Castiel, who’s looking more than a little pink in the cheeks at the tender gesture. “You want me to say it out loud?” Castiel nods, cautiously, though he isn’t quite sure what Dean’s talking about. “Alright then. I love you, Castiel Novak. I have for the past eight years, and I’m pretty sure that means I’m stuck loving you for the rest of my life.”

Castiel smiles widely, and he knows he wouldn’t be able to tamp it down even if he wanted to. “I love you too, Dean Winchester.”

They stare at each other, like a couple of lovestruck fools, for a few long moments before Dean starts tugging Castiel’s hand, trying to get the bar owner to lean over the bar top. “Get over here and kiss me, you big sap.”

Castiel hums softly, leaning into Dean only to meet him halfway. “With pleasure, Mister Winchester.”

**Notes for the Chapter:**

> p.s. in case anyone wants to know, the way that dean and lisa met was actually super random. i thought about putting it in, and then i realized it wasn't important enough.  
> anyway, they basically met after dean left pontiac and went back to lawrence (i know, shut up) and told lisa's dad that he couldn't find her. they run into each other on the street, and then again at the grocery story, and then again somehwere else. somehow beyond that, they end up friends and then dating and then engaged until they get here. ta da  
> also, yes, i believe lisa would be one of those people to name her son after her father  
> EDIT 12/6/17: so i started to write the epilogue and then i realized it really didn't say anything that i wanted to add to this story, not to mention the fact that it's been over a month and i've been involved in other school shit, so i'm scrapping the epilogue idea and just leave it as is. thanks for reading through and be sure to leave a comment :)

**Author's Note:**

> come find me on tumblr for either [supernatural](angeloflightclaire.tumblr.com) or [general fandom shit](sky-of-starflowers.tumblr.com)
> 
> if you want you can find the original, shittier version of this story [here](https://www.fanfiction.net/s/9877253/1/Of-All-The-Bars)
> 
> also, any and all critiques/kudos/comments/random ass shit is welcome and encouraged!


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